dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-93f716b9422a462f92829409b20246e1 | CCOCCBr.Clc1ncnc2cc(-c3ccco3)[nH]c12>>CCOCCn1c(-c2ccco2)cc2ncnc(Cl)c21 | O.ClC=1C2=C(N=CN1)C=C(N2)C=2OC=CC2.C([O-])([O-])=O.[Cs+].[Cs+].C([O-])([O-])=O.[Cs+].[Cs+].C(C)OCCBr.C(C)OCCBr>>ClC=1C2=C(N=CN1)C=C(N2CCOCC)C=2OC=CC2 | Br[CH2:5][CH2:4][O:3][CH2:2][CH3:1].[nH:6]1[c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[cH:13][c:14]2[n:15][cH:16][n:17][c:18]([Cl:19])[c:20]12>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][n:6]1[c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[cH:13][c:14]2[n:15][cH:16][n:17][c:18]([Cl:19])[c:20]12 | CCOCCBr.Clc1ncnc2cc(-c3ccco3)[nH]c12 | CCOCCn1c(-c2ccco2)cc2ncnc(Cl)c21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e9fbaa0885668a0db6604d7955d2895802f0f03f498828bb48474e6359c120b7 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1coc(-c2cc3ncncc3[nH]2)c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[#8;a:4]:[c:5]-[c:6]1:[c:7]:[c:8]2:[#7;a:9]:[c:10]:[#7;a:11]:[c:12](-[Cl;D1;H0:13]):[c:14]:2:[nH;D2;+0:15]:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:15]1:[c:14]2:[c:8](:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2-[Cl;D1;H0:13]):[c:7]:[c:6]:1-[c:5]:[#8;a:4] | null | [] | null | null | null | null | To a solution of 4-chloro-6-(2-furyl)-5H-pyrrolo[3,2-d]pyrimidine (220 mg) in N,N-dimethylformamide (1.2 mL) was added cesium carbonate (489 mg) under ice-cooling, and the mixture was stirred under ice-cooling for 15 min. 2-Bromoethyl ethyl ether (0.169 mL) was added and the mixture was stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1cc2ncncc2[nH]1 | c1ccoc1.c1cc2ncncc2[nH]1 | HBr | CN(C=O)C | null | null | CCOCCBr.Clc1ncnc2cc(-c3ccco3)[nH]c12>CN(C=O)C>CCOCCn1c(-c2ccco2)cc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da144fcb7f254543bff93793120ab243 | CCOCCn1c(-c2ccco2)cc2ncnc(Cl)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1>>CCOCCn1c(-c2ccco2)cc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 | C(O)([O-])=O.[Na+].ClC=1C2=C(N=CN1)C=C(N2CCOCC)C=2OC=CC2.CC=1C=C(N)C=CC1OC=1C=NC(=CC1)C.CN1C(CCC1)=O>>C(C)OCCN1C(=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C)C=2OC=CC2 | Cl[c:18]1[n:17][cH:16][n:15][c:14]2[cH:13][c:7](-[c:8]3[cH:9][cH:10][cH:11][o:12]3)[n:6]([CH2:5][CH2:4][O:3][CH2:2][CH3:1])[c:35]21.[NH2:19][c:20]1[cH:21][cH:22][c:23]([O:24][c:25]2[cH:26][cH:27][c:28]([CH3:29])[n:30][cH:31]2)[c:32]([CH3:33])[cH:34]1>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][n:6]1[c:7](-[c:8]2[cH:9][cH:10][cH... | CCOCCn1c(-c2ccco2)cc2ncnc(Cl)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1 | CCOCCn1c(-c2ccco2)cc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 | null | null | O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | a761a23478bcca0adfe0c4dd4341ad165c5bf801aa5c397f8a3fb7ad8077557d | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(Oc2ccc(Nc3ncnc4cc(-c5ccco5)[nH]c34)cc2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 63.8 | [{"value": 63.8, "product": "C(C)OCCN1C(=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C)C=2OC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 2 | HOUR | A mixture of 4-chloro-5-(2-ethoxyethyl)-6-(2-furyl)-5H-pyrrolo[3,2-d]pyrimidine (76 mg), 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (67 mg) and 1-methyl-2-pyrrolidinone (1.5 mL) was stirred at 140° C. for 2 hrs, poured into water (8 mL) and adjusted to pH 8 with saturated aqueous sodium hydrogen carbonate. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cc2ncncc2[nH]1 | c1cc2ncncc2[nH]1 | c1ccoc1.c1cc2ncncc2[nH]1.c1ccccc1.c1ccncc1 | HCl | O | 140 | 2 | CCOCCn1c(-c2ccco2)cc2ncnc(Cl)c21.Cc1ccc(Oc2ccc(N)cc2C)cn1>O>CCOCCn1c(-c2ccco2)cc2ncnc(Nc3ccc(Oc4ccc(C)nc4)c(C)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-819695785614457faa55f55bf57bc999 | Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccc(C(=O)O)cc5)[nH]c34)cc2C)cn1>>Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccc(CO)cc5)[nH]c34)cc2C)cn1 | [BH4-].[Na+].C(C)N(CC)CC.CC=1C=C(C=CC1OC=1C=NC(=CC1)C)NC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C(=O)O)C=C2.C(=O)(N1C=NC=C1)N1C=NC=C1>>CC=1C=C(C=CC1OC=1C=NC(=CC1)C)NC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C=C2)CO | O=[C:23]([c:22]1[cH:21][cH:20][c:19](-[c:18]2[cH:17][c:16]3[n:15][cH:14][n:13][c:12]([NH:11][c:10]4[cH:9][cH:8][c:7]([O:6][c:5]5[cH:4][cH:3][c:2]([CH3:1])[n:33][cH:32]5)[c:30]([CH3:31])[cH:29]4)[c:28]3[nH:27]2)[cH:26][cH:25]1)[OH:24]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[n:13][cH:... | Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccc(C(=O)O)cc5)[nH]c34)cc2C)cn1 | Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccc(CO)cc5)[nH]c34)cc2C)cn1 | null | null | O1CCCC1.O.CO | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc(-c2cc3ncnc(Nc4ccc(Oc5cccnc5)cc4)c3[nH]2)cc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 55 | [{"value": 55.0, "product": "CC=1C=C(C=CC1OC=1C=NC(=CC1)C)NC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C=C2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a suspension of 4-[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-6-yl]benzoic acid (122 mg) in tetrahydrofuran (10 mL) was added triethylamine (30.5 mg) and, after stirring at room temperature for 10 min, 1,1′-carbonyldiimidazole (49 mg) was added, and the mixture was stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccncc1.c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1 | Other | O1CCCC1.O.CO | null | 0.166667 | Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccc(C(=O)O)cc5)[nH]c34)cc2C)cn1>O1CCCC1.O.CO>Cc1ccc(Oc2ccc(Nc3ncnc4cc(-c5ccc(CO)cc5)[nH]c34)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-60bb1591e157493d9fbad4f722086143 | Nc1c(I)ncnc1I.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>Nc1c(I)ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | NC=1C(=NC=NC1I)I.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F.O>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC1=NC=NC(=C1N)I | I[c:8]1[c:2]([NH2:1])[c:3]([I:4])[n:5][cH:6][n:7]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][c:20]([F:21])[cH:22]2)[c:23]([Cl:24])[cH:25]1>>[NH2:1][c:2]1[c:3]([I:4])[n:5][cH:6][n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][c:20]([F:21])[cH:22]... | Nc1c(I)ncnc1I.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | Nc1c(I)ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ccncn3)cc2)cc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[I;D1;H0:6]):[c:7]:1-[N;D1;H2:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[I;D1;H0:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:7]:1-[N;D1;H2:8] | 81 | [{"value": 81.0, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC1=NC=NC(=C1N)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-amino-4,6-diiodopyrimidine (3.83 g) and 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (2.78 g) in 1-methyl-2-pyrrolidone (30 mL) was stirred at 70° C. for 14 hrs. Water was added to the reaction system and the mixture was extracted with ethyl acetate. The organic layer washed with water and saturated brine an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HI | CN1C(CCC1)=O | null | null | Nc1c(I)ncnc1I.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>CN1C(CCC1)=O>Nc1c(I)ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-461d0e46abd14a6b88e2ca159a97d614 | Nc1c(C#CCNC(=O)[O-])ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>CC(C)(C)OC(=O)NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | NC=1C(=NC=NC1NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl)C#CCNC([O-])=O>>C(C)(C)(C)OC(NCC1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl)=O | [C:1](#[C:10][CH2:9][NH:8][C:6]([O-:5])=[O:7])[c:12]1[n:13][cH:14][n:15][c:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]3)[c:31]([Cl:32])[cH:33]2)[c:34]1[NH2:35]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][c:12]2[n:13][cH:14][n:15... | Nc1c(C#CCNC(=O)[O-])ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | CC(C)(C)OC(=O)NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | null | [Cu]I | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 693957d2ee58f43bcbe694db54ffef8891f11bce20cfded472d0966f7d3c4d36 | dc144c1e758c04b5eb62f81ce219ee8d43b8cebd872353ca8711ad8a6062d5ce | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c;H0;D3;+0:6](-[C;H0;D2;+0:7]#[C;H0;D2;+0:8]-[C:9]-[#7:10]-[C:11](-[O-;H0;D1:12])=[O;D1;H0:13]):[c:14]:1-[NH2;D1;+0:15]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c;H0;D3;+0:6]2:[c:16]:[c;H0;D3;+0:8](-[C:9]-[#7:10]-[C:11](=[O;D1;H0:13])-[O;H0;D2;+0:12]-[C:17](-[C;D1;H3:18])(-[C;D1;H3... | 148.5 | [{"value": 148.5, "product": "C(C)(C)(C)OC(NCC1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 12 | HOUR | A mixture of tert-butyl (3-[5-amino-6-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)pyrimidin-4-yl]prop-2-ynylcarbamate (720 mg) and copper(I) iodide (55.2 mg) in N,N-dimethylformamide (7.0 mL) was stirred at 80° C. for 12 hrs. After concentration under reduced pressure, the residue was separated and purified by colum... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic acid.Primary amine.Alkyne | Carbamic ester.Ether.Boc | c1cncnc1 | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1.c1ccccc1.c1ccccc1 | null | [Cu]I.CN(C=O)C | 80 | 12 | Nc1c(C#CCNC(=O)[O-])ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>[Cu]I.CN(C=O)C>CC(C)(C)OC(=O)NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df99aae6eb6d4398afa663d1b74d2106 | CC(C)(C)OC(=O)NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1>>Cl.NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | C(C)O.C(C)(C)(C)OC(NCC1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl)=O.Cl>>Cl.Cl.NCC1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl | CC(C)(C)OC(=O)[NH:3][CH2:4][c:5]1[cH:6][c:7]2[n:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]4[cH:20][cH:21][cH:22][c:23]([F:24])[cH:25]4)[c:26]([Cl:2])[cH:28]3)[c:29]2[nH:30]1>>[ClH:2].[NH2:3][CH2:4][c:5]1[cH:6][c:7]2[n:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([O:17][CH2:1... | CC(C)(C)OC(=O)NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | Cl.NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | null | null | O1CCCC1 | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | f9b0ddd5e086b40f0768881f9b226acdc5a9dc29f99a9283af567e925b55a3d7 | b15a28c2a3fd58b98c3a6c1b435f8c25519aeb02339cc9ac8ff8fecd35099d5c | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[c:3]:[#7;a:4].[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[Cl;H0;D1;+0:9]):[c:10]:[c:11]>>[#7;a:4]:[c:3]-[C:2]-[NH2;D1;+0:1].[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[Cl;D1;H0:12]):[c:10]:[c:11].[ClH;D0;+0:9] | null | [] | 60 | CELSIUS | 2 | HOUR | To a solution of tert-butyl[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-6-yl]methylcarbamate (500 mg) in tetrahydrofuran (12 mL) was added 2N hydrochloric acid (6.0 mL) at room temperature. The mixture was stirred at 60° C. for 2 hrs, ethanol was added to the reaction system and the mix... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boc | Aromatic halide.Primary amine | c1ccccc1 | c1ccccc1 | c1ncc2[nH]ccc2n1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | 60 | 2 | CC(C)(C)OC(=O)NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1>O1CCCC1>Cl.NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e8b188d8ae246efa8394b9e9afb8114 | CN(C)C/C=C/C(=O)O.NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1>>CN(C)C/C=C/C(=O)NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | Cl.Cl.NCC1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl.Cl.CN(C/C=C/C(=O)O)C.Cl.C(C)N=C=NCCCN(C)C.O.ON1N=NC2=C1C=CC=C2>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2)CNC(\C=C\CN(C)C)=O | O[C:7](/[CH:6]=[CH:5]/[CH2:4][N:2]([CH3:1])[CH3:3])=[O:8].[NH2:9][CH2:10][c:11]1[cH:12][c:13]2[n:14][cH:15][n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]4[cH:26][cH:27][cH:28][c:29]([F:30])[cH:31]4)[c:32]([Cl:33])[cH:34]3)[c:35]2[nH:36]1>>[CH3:1][N:2]([CH3:3])[CH2:4]/[CH:5]=[CH:6]/[C:7](=[O:8])[NH... | CN(C)C/C=C/C(=O)O.NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | CN(C)C/C=C/C(=O)NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | null | null | O.C(C)N(CC)CC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[C:5]-[#7:6].[#7;a:7]:[c:8]-[C:9]-[NH2;D1;+0:10]>>[#7:6]-[C:5]/[C:4]=[C:3]/[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]-[c:8]:[#7;a:7] | 64.3 | [{"value": 64.3, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2)CNC(\\C=C\\CN(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-(aminomethyl)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (150 mg), (2E)-4-(dimethylamino)but-2-enoic acid hydrochloride (105 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (244 mg), 1-hydroxybenzotriazole monohydrate (196 mg) and triet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ncc2[nH]ccc2n1.c1ccccc1.c1ccccc1 | HO- | O.C(C)N(CC)CC.CN(C=O)C | null | null | CN(C)C/C=C/C(=O)O.NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1>O.C(C)N(CC)CC.CN(C=O)C>CN(C)C/C=C/C(=O)NCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac05d5a454f148bd9711858934e1c9f2 | COCC(=O)O.Nc1ccc(-c2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3[nH]2)cc1>>COCC(=O)Nc1ccc(-c2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3[nH]2)cc1 | NC1=CC=C(C=C1)C1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl.COCC(=O)O.Cl.C(C)N=C=NCCCN(C)C.O.ON1N=NC2=C1C=CC=C2.COCC(=O)O.Cl.C(C)N=C=NCCCN(C)C.O.ON1N=NC2=C1C=CC=C2>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C=C2)NC(COC)=O | O[C:4]([CH2:3][O:2][CH3:1])=[O:5].[NH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][c:13]3[n:14][cH:15][n:16][c:17]([NH:18][c:19]4[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]5[cH:26][cH:27][cH:28][c:29]([F:30])[cH:31]5)[c:32]([Cl:33])[cH:34]4)[c:35]3[nH:36]2)[cH:37][cH:38]1>>[CH3:1][O:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[cH:8... | COCC(=O)O.Nc1ccc(-c2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3[nH]2)cc1 | COCC(=O)Nc1ccc(-c2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3[nH]2)cc1 | null | null | O.C(C)N(CC)CC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(COc2ccc(Nc3ncnc4cc(-c5ccccc5)[nH]c34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 54.9 | [{"value": 54.9, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2)C2=CC=C(C=C2)NC(COC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of 6-(4-aminophenyl)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine (100 mg), methoxyacetic acid (29.4 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (94 mg), 1-hydroxybenzotriazole monohydrate (75 mg) and triethylamine (0.23 mL) in N,N-dimethylformamide (5 mL... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ncc2[nH]ccc2n1.c1ccccc1.c1ccccc1 | HO- | O.C(C)N(CC)CC.CN(C=O)C | null | 24 | COCC(=O)O.Nc1ccc(-c2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3[nH]2)cc1>O.C(C)N(CC)CC.CN(C=O)C>COCC(=O)Nc1ccc(-c2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3[nH]2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0a2b5f3923741ff9192ba6e69b1b3df | C#CCCCO.Nc1c(I)ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>Nc1c(C#CCCCO)ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC1=NC=NC(=C1N)I.C(CCC#C)O.C(CCC#C)O>>NC=1C(=NC=NC1NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl)C#CCCCO | [CH:4]#[C:5][CH2:6][CH2:7][CH2:8][OH:9].I[c:3]1[c:2]([NH2:1])[c:13]([NH:14][c:15]2[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]3[cH:22][cH:23][cH:24][c:25]([F:26])[cH:27]3)[c:28]([Cl:29])[cH:30]2)[n:12][cH:11][n:10]1>>[NH2:1][c:2]1[c:3]([C:4]#[C:5][CH2:6][CH2:7][CH2:8][OH:9])[n:10][cH:11][n:12][c:13]1[NH:14][c:15]1[cH:16][... | C#CCCCO.Nc1c(I)ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | Nc1c(C#CCCCO)ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)#N.C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 6c841971a35ffd50215936cda19c192218792b140679c95a1b7a8fa56d8a741b | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc(COc2ccc(Nc3ccncn3)cc2)cc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[N;D1;H2:8].[C:9]-[C:10]#[CH;D1;+0:11]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:11]#[C:10]-[C:9]):[c:7]:1-[N;D1;H2:8] | 57.8 | [{"value": 57.8, "product": "NC=1C(=NC=NC1NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl)C#CCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of N4-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-iodopyrimidine-4,5-diamine (300 mg) and 4-pentyn-1-ol (65 mg) in acetonitrile-triethylamine (6.0 mL-4.5 mL) were added bis(triphenylphosphine)palladium(II) dichloride (22.5 mg) and copper(I) iodide (7.3 mg) at room temperature, and the mixture was stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC | null | 24 | C#CCCCO.Nc1c(I)ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)#N.C(C)N(CC)CC>Nc1c(C#CCCCO)ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3962d9448bd1490eb0f5b55adfc664ae | Nc1c(C#CCCCO)ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>OCCCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | NC=1C(=NC=NC1NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl)C#CCCCO>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2)CCCO | [OH:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][c:7]1[n:8][cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][c:23]([F:24])[cH:25]3)[c:26]([Cl:27])[cH:28]2)[c:29]1[NH2:30]>>[OH:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][c:7]2[n:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([O:17][... | Nc1c(C#CCCCO)ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | OCCCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | null | [Cu]I | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 4074b4d15ae59e43a9db38b88971d3da4bc2c5011d6f413a05bb8fbb5a5c4621 | f32b9a5ecc70d866a53cd56f9bc47b365771cdcbb02563cae8c78e4de228d870 | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[C;H0;D2;+0:7]#[C;H0;D2;+0:8]-[C:9]-[C:10]):[c:11]:1-[NH2;D1;+0:12]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C:9]-[C:10]):[nH;D2;+0:12]:[c:11]:1:2 | 68 | [{"value": 68.0, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2)CCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 5 | HOUR | A mixture of 5-[5-amino-6-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)pyrimidin-4-yl]pent-4-yn-1-ol (140 mg) and copper(I) iodide (19 mg) in N,N-dimethylformamide (2.0 mL) was stirred at 80° C. for 5 hrs. After concentration under reduced pressure, the residue was separated and purified by column chromatography (bas... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Alkyne | null | c1cncnc1 | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1.c1ccccc1.c1ccccc1 | null | [Cu]I.CN(C=O)C | 80 | 5 | Nc1c(C#CCCCO)ncnc1Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>[Cu]I.CN(C=O)C>OCCCc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-384d4ceaf3924d91940bade29e73cd1e | CC(C)(C)OC(=O)NC/C=C/c1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1>>NC/C=C/c1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | [OH-].[Na+].ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2)/C=C/CNC(OC(C)(C)C)=O.Cl>>NC/C=C/C1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl | CC(C)(C)OC(=O)[NH:1][CH2:2]/[CH:3]=[CH:4]/[c:5]1[cH:6][c:7]2[n:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]4[cH:20][cH:21][cH:22][c:23]([F:24])[cH:25]4)[c:26]([Cl:27])[cH:28]3)[c:29]2[nH:30]1>>[NH2:1][CH2:2]/[CH:3]=[CH:4]/[c:5]1[cH:6][c:7]2[n:8][cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH... | CC(C)(C)OC(=O)NC/C=C/c1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | NC/C=C/c1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 | null | null | O1CCCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]/[C:3]=[C:4]/[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]/[C:4]=[C:3]/[C:2]-[NH2;D1;+0:1] | 85.7 | [{"value": 85.7, "product": "NC/C=C/C1=CC=2N=CN=C(C2N1)NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | To a solution of tert-butyl (2E)-3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-6-yl]prop-2-enylcarbamate (150 mg) in tetrahydrofuran (6.0 mL) was added 2N hydrochloric acid (3.0 mL) at room temperature and the mixture was stirred at 60° C. for 2 hrs. 1N Aqueous sodium hydroxide solutio... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ncc2[nH]ccc2n1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | 60 | 2 | CC(C)(C)OC(=O)NC/C=C/c1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1>O1CCCC1>NC/C=C/c1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97034edf65a147cf9ffe896e1c20c09c | CSc1ncnc2cn[nH]c12.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>Fc1cccc(COc2ccc(Nc3ncnc4cn[nH]c34)cc2Cl)c1 | CSC=1C2=C(N=CN1)C=NN2.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F.Cl.N1=CC=CC=C1>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=NN2 | CS[c:14]1[n:15][cH:16][n:17][c:18]2[cH:19][n:20][nH:21][c:22]12.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:23][c:24]2[Cl:25])[cH:26]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH:13][c:14]3[n:15][cH:16][n:17][c:18]4[cH:19][n:20][nH:21][c:22]3... | CSc1ncnc2cn[nH]c12.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | Fc1cccc(COc2ccc(Nc3ncnc4cn[nH]c34)cc2Cl)c1 | null | null | CN1C(CCC1)=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 4801922deca49a73697a62fd7fab1747543ee99ec6fb977938c2679daa69e0aa | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1ccc(COc2ccc(Nc3ncnc4cn[nH]c34)cc2)cc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 66 | [{"value": 61.0, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=NN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=NN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 10 | HOUR | A mixture of 7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine (known compound from literature: J. Am. Chem. Soc., 1956, 78, 2418) (150 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (227 mg) and pyridine hydrochloride (156 mg) in 1-methyl-2-pyrrolidone (3 mL) was stirred at 120° C. for 10 hrs. After the completion of the reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1ncc2n[nH]cc2n1 | c1ncc2n[nH]cc2n1 | c1ccccc1.c1ccccc1.c1ncc2n[nH]cc2n1 | Other | CN1C(CCC1)=O.C(C)(=O)OCC | 120 | 10 | CSc1ncnc2cn[nH]c12.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>CN1C(CCC1)=O.C(C)(=O)OCC>Fc1cccc(COc2ccc(Nc3ncnc4cn[nH]c34)cc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-408ccb2c239a484ba584825e5db25fee | COC(=O)c1ccc(Cn2ncc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1>>O=C(O)c1ccc(Cn2ncc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 | ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=NN2CC2=CC=C(C(=O)OC)C=C2.O1CCCC1.CO.[OH-].[Na+].Cl>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=NN2CC2=CC=C(C(=O)O)C=C2 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([CH2:8][n:9]2[n:10][cH:11][c:12]3[n:13][cH:14][n:15][c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]5[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]5)[c:31]([Cl:32])[cH:33]4)[c:34]23)[cH:35][cH:36]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][n:9]2[n:10][cH:11... | COC(=O)c1ccc(Cn2ncc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 | O=C(O)c1ccc(Cn2ncc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccc(Nc3ncnc4cnn(Cc5ccccc5)c34)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 65.8 | [{"value": 65.8, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=NN2CC2=CC=C(C(=O)O)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of methyl 4-{[7-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]methyl}benzoate (25 mg) in a mixed solvent of tetrahydrofuran/methanol (1:1, 1 mL) was added 1N aqueous sodium hydroxide solution (0.5 mL), and the mixture was stirred at room temperature for 1 hr. After the c... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ncnc2cn[nH]c12.c1ccccc1.c1ccccc1 | Other | O | null | 1 | COC(=O)c1ccc(Cn2ncc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1>O>O=C(O)c1ccc(Cn2ncc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-21dfc728679b4a809a02cd3164de8da7 | COCCN.O=C(O)c1ccc(Cn2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1>>COCCNC(=O)c1ccc(Cn2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1 | ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C=2C(N=CN1)=CN(N2)CC2=CC=C(C(=O)O)C=C2.COCCN.ON1N=NC2=C1C=CC=C2.Cl.CN(CCCN=C=NCC)C>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C=2C(N=CN1)=CN(N2)CC2=CC=C(C(=O)NCCOC)C=C2 | [CH3:1][O:2][CH2:3][CH2:4][NH2:5].O[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([CH2:12][n:13]2[cH:14][c:15]3[n:16][cH:17][n:18][c:19]([NH:20][c:21]4[cH:22][cH:23][c:24]([O:25][CH2:26][c:27]5[cH:28][cH:29][cH:30][c:31]([F:32])[cH:33]5)[c:34]([Cl:35])[cH:36]4)[c:37]3[n:38]2)[cH:39][cH:40]1>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:... | COCCN.O=C(O)c1ccc(Cn2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1 | COCCNC(=O)c1ccc(Cn2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1 | null | null | C(C)N(CC)CC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(COc2ccc(Nc3ncnc4cn(Cc5ccccc5)nc34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 229.5 | [{"value": 229.5, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C=2C(N=CN1)=CN(N2)CC2=CC=C(C(=O)NCCOC)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-{[7-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-2H-pyrazolo[4,3-d]pyrimidin-2-yl]methyl}benzoic acid (45 mg), 2-methoxyethylamine (9 mg), 1-hydroxybenzotriazole (18 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (26 mg) and triethylamine (0.08 mL) in N,N-dimethylformamide (2 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ncnc2c[nH]nc12.c1ccccc1.c1ccccc1 | HO- | C(C)N(CC)CC.CN(C=O)C | null | null | COCCN.O=C(O)c1ccc(Cn2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1>C(C)N(CC)CC.CN(C=O)C>COCCNC(=O)c1ccc(Cn2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3695b16b65e44800aa8c0af10d9082ed | CSc1ncnc2cn[nH]c12.O=[N+]([O-])c1ccc(F)cc1>>CSc1ncnc2cn(-c3ccc([N+](=O)[O-])cc3)nc12 | O.FC1=CC=C(C=C1)[N+](=O)[O-].CSC=1C2=C(N=CN1)C=NN2.CC(C)([O-])C.[K+]>>CSC=1C=2C(N=CN1)=CN(N2)C2=CC=C(C=C2)[N+](=O)[O-] | [CH3:1][S:2][c:3]1[n:4][cH:5][n:6][c:7]2[cH:8][n:9][nH:19][c:20]12.F[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][n:6][c:7]2[cH:8][n:9](-[c:10]3[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]3)[n:19][c:20]12 | CSc1ncnc2cn[nH]c12.O=[N+]([O-])c1ccc(F)cc1 | CSc1ncnc2cn(-c3ccc([N+](=O)[O-])cc3)nc12 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 24d6970b2e7905aed62cd13b1b10c73fc1ef6567b39c1acf2f9bb3e0e7cd7f12 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2cc3ncncc3n2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#16:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[n;H0;D2;+0:13]:[nH;D2;+0:14]:[c:15]:1:2>>[#16:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[n;H0;D3;+0:13](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[n;H0;D2;+0:14]:[c:15]:1:2 | 99.5 | [{"value": 99.5, "product": "CSC=1C=2C(N=CN1)=CN(N2)C2=CC=C(C=C2)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine (500 mg) in N,N-dimethylformamide (10 mL) was added potassium tert-butoxide (405 mg) under ice-cooling, and the mixture was stirred at room temperature for 10 min. Subsequently, 1-fluoro-4-nitrobenzene (465 mg) was added, and the mixture was stirred at 70° C.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ncc2n[nH]cc2n1.c1ccccc1 | c1ncnc2c[nH]nc12.c1ccccc1 | c1ncnc2c[nH]nc12.c1ccccc1 | HF | CN(C=O)C | null | 0.166667 | CSc1ncnc2cn[nH]c12.O=[N+]([O-])c1ccc(F)cc1>CN(C=O)C>CSc1ncnc2cn(-c3ccc([N+](=O)[O-])cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74ca871001d74c068b927baa09bfec03 | Cc1ccc(Oc2ccc(Nc3ncnc4cn(-c5ccc([N+](=O)[O-])cc5)nc34)cc2C)cn1>>Cc1ccc(Oc2ccc(Nc3ncnc4cn(-c5ccc(N)cc5)nc34)cc2C)cn1 | CC=1C=C(C=CC1OC=1C=NC(=CC1)C)NC=1C=2C(N=CN1)=CN(N2)C2=CC=C(C=C2)[N+](=O)[O-].[Cl-].[Ca+2].[Cl-]>>NC1=CC=C(C=C1)N1N=C2C(N=CN=C2NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C)=C1 | O=[N+:23]([O-])[c:22]1[cH:21][cH:20][c:19](-[n:18]2[cH:17][c:16]3[n:15][cH:14][n:13][c:12]([NH:11][c:10]4[cH:9][cH:8][c:7]([O:6][c:5]5[cH:4][cH:3][c:2]([CH3:1])[n:32][cH:31]5)[c:29]([CH3:30])[cH:28]4)[c:27]3[n:26]2)[cH:25][cH:24]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[n:13][cH:14]... | Cc1ccc(Oc2ccc(Nc3ncnc4cn(-c5ccc([N+](=O)[O-])cc5)nc34)cc2C)cn1 | Cc1ccc(Oc2ccc(Nc3ncnc4cn(-c5ccc(N)cc5)nc34)cc2C)cn1 | null | null | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-n2cc3ncnc(Nc4ccc(Oc5cccnc5)cc4)c3n2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 75 | [{"value": 75.0, "product": "NC1=CC=C(C=C1)N1N=C2C(N=CN=C2NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C)=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 10 | MINUTE | To a solution of N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}-2-(4-nitrophenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-amine (200 mg) in a mixed solvent of ethanol/water (9:1, 6 mL) was added calcium chloride (90%, 28 mg) and the mixture was stirred at 100° C. for 10 min. Reduced iron (90%, 164 mg) was added at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccccc1.c1ncnc2c[nH]nc12.c1ccccc1 | Other | C(C)O.O | 100 | 0.166667 | Cc1ccc(Oc2ccc(Nc3ncnc4cn(-c5ccc([N+](=O)[O-])cc5)nc34)cc2C)cn1>C(C)O.O>Cc1ccc(Oc2ccc(Nc3ncnc4cn(-c5ccc(N)cc5)nc34)cc2C)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b4baa0c51a64f5cbaae72595b2c1da1 | COC(=O)c1ccc(F)cc1.CSc1ncnc2cn[nH]c12>>COC(=O)c1ccc(-n2cc3ncnc(SC)c3n2)cc1 | O.CSC=1C2=C(N=CN1)C=NN2.FC1=CC=C(C(=O)OC)C=C1.C([O-])([O-])=O.[K+].[K+]>>CSC=1C=2C(N=CN1)=CN(N2)C2=CC=C(C(=O)OC)C=C2 | F[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:21][cH:20]1.[n:9]1[cH:10][c:11]2[n:12][cH:13][n:14][c:15]([S:16][CH3:17])[c:18]2[nH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[n:9]2[cH:10][c:11]3[n:12][cH:13][n:14][c:15]([S:16][CH3:17])[c:18]3[n:19]2)[cH:20][cH:21]1 | COC(=O)c1ccc(F)cc1.CSc1ncnc2cn[nH]c12 | COC(=O)c1ccc(-n2cc3ncnc(SC)c3n2)cc1 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | 24d6970b2e7905aed62cd13b1b10c73fc1ef6567b39c1acf2f9bb3e0e7cd7f12 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2cc3ncncc3n2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#16:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[n;H0;D2;+0:13]:[nH;D2;+0:14]:[c:15]:2:1>>[#16:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[n;H0;D3;+0:13](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[n;H0;D2;+0:14]:[c:15]:2:1 | 49.8 | [{"value": 49.8, "product": "CSC=1C=2C(N=CN1)=CN(N2)C2=CC=C(C(=O)OC)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 3 | HOUR | To a solution of 7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine (100 mg) and methyl 4-fluorobenzoate (102 mg) in 1-methyl-2-pyrrolidone (2 mL) was added potassium carbonate (125 mg), and the mixture was stirred at 120° C. for 3 hrs. After the completion of the reaction, water was added to the reaction mixture and the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ncc2n[nH]cc2n1 | c1ccccc1.c1ncnc2c[nH]nc12 | c1ccccc1.c1ncnc2c[nH]nc12 | HF | CN1C(CCC1)=O | 120 | 3 | COC(=O)c1ccc(F)cc1.CSc1ncnc2cn[nH]c12>CN1C(CCC1)=O>COC(=O)c1ccc(-n2cc3ncnc(SC)c3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62f69f7064a94048a73f43c634f66abd | O=Cc1ccc(-n2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1>>OCc1ccc(-n2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1 | ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C=2C(N=CN1)=CN(N2)C2=CC=C(C=O)C=C2.[BH4-].[Na+]>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C=2C(N=CN1)=CN(N2)C2=CC=C(C=C2)CO | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][c:9]3[n:10][cH:11][n:12][c:13]([NH:14][c:15]4[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]5[cH:22][cH:23][cH:24][c:25]([F:26])[cH:27]5)[c:28]([Cl:29])[cH:30]4)[c:31]3[n:32]2)[cH:33][cH:34]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][c:9]3[n:10][cH:11][n:12][c:13]([... | O=Cc1ccc(-n2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1 | OCc1ccc(-n2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1 | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(COc2ccc(Nc3ncnc4cn(-c5ccccc5)nc34)cc2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 39.8 | [{"value": 39.8, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C=2C(N=CN1)=CN(N2)C2=CC=C(C=C2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 4-[7-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-2H-pyrazolo[4,3-d]pyrimidin-2-yl]benzaldehyde (50 mg) in methanol (2 mL) was added sodium borohydride (2 mg) under ice-cooling, and the mixture was stirred for 30 min. After the completion of the reaction, the reaction solution was concentrated under... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.c1ncnc2c[nH]nc12.c1ccccc1.c1ccccc1 | null | CO | null | 0.5 | O=Cc1ccc(-n2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1>CO>OCc1ccc(-n2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d6e77701d014150b9dbb8d685c09bbe | CS(=O)(=O)CCN.O=Cc1ccc(-n2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1>>CS(=O)(=O)CCNCc1ccc(-n2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1 | C(O)([O-])=O.[Na+].ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C=2C(N=CN1)=CN(N2)C2=CC=C(C=O)C=C2.Cl.CS(=O)(=O)CCN.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C=2C(N=CN1)=CN(N2)C2=CC=C(C=C2)CNCCS(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][NH2:7].O=[CH:8][c:9]1[cH:10][cH:11][c:12](-[n:13]2[cH:14][c:15]3[n:16][cH:17][n:18][c:19]([NH:20][c:21]4[cH:22][cH:23][c:24]([O:25][CH2:26][c:27]5[cH:28][cH:29][cH:30][c:31]([F:32])[cH:33]5)[c:34]([Cl:35])[cH:36]4)[c:37]3[n:38]2)[cH:39][cH:40]1>>[CH3:1][S:2](=[O:3])(=[O:4])[CH... | CS(=O)(=O)CCN.O=Cc1ccc(-n2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1 | CS(=O)(=O)CCNCc1ccc(-n2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1 | null | null | C(C)(=O)O.CN(C=O)C | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(COc2ccc(Nc3ncnc4cn(-c5ccccc5)nc34)cc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 71.4 | [{"value": 71.4, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C=2C(N=CN1)=CN(N2)C2=CC=C(C=C2)CNCCS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4-[7-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-2H-pyrazolo[4,3-d]pyrimidin-2-yl]benzaldehyde (80 mg) and 2-(methylsulfonyl)ethylamine hydrochloride (40 mg) in N,N-dimethylformamide (2 mL) was added acetic acid (0.02 mL), and the mixture was stirred at room temperature for 1 hr. Subsequently, sodi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ncnc2c[nH]nc12.c1ccccc1.c1ccccc1 | Other | C(C)(=O)O.CN(C=O)C | null | 1 | CS(=O)(=O)CCN.O=Cc1ccc(-n2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1>C(C)(=O)O.CN(C=O)C>CS(=O)(=O)CCNCc1ccc(-n2cc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-892b952a162e49deb2fae1d8da859cbc | OCCn1ncc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21>>Fc1cccc(COc2ccc(N3CCn4ncc5ncnc3c54)cc2Cl)c1 | O.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=NN2CCO.N(=NC(=O)N1CCCCC1)C(=O)N1CCCCC1.C(CCC)P(CCCC)CCCC>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)N1CCN2C3=C(N=CN=C13)C=N2 | O[CH2:14][CH2:15][n:16]1[n:17][cH:18][c:19]2[n:20][cH:21][n:22][c:23]([NH:13][c:12]3[cH:11][cH:10][c:9]([O:8][CH2:7][c:6]4[cH:5][cH:4][cH:3][c:2]([F:1])[cH:28]4)[c:26]([Cl:27])[cH:25]3)[c:24]12>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][n:16]4[n:17][cH:18][c:19]5[... | OCCn1ncc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | Fc1cccc(COc2ccc(N3CCn4ncc5ncnc3c54)cc2Cl)c1 | null | null | O1CCCC1.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 57ea5a23f177ce0b54ee8bc004f91ae93ec31d6506c262f2a2851bf863f00685 | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | c1ccc(COc2ccc(N3CCn4ncc5ncnc3c54)cc2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[#7;a:3]1:[#7;a:4]:[c:5]:[c:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:15]:1:2>>[c:13]:[c:12](-[N;H0;D3;+0:11]1-[CH2;D2;+0:1]-[C:2]-[#7;a:3]2:[#7;a:4]:[c:5]:[c:6]3:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]-1:[c:15]:2:3):[c:14] | 81 | [{"value": 81.0, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)N1CCN2C3=C(N=CN=C13)C=N2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-[7-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]ethanol (40 mg), 1,1′-(azodicarbonyl)dipiperidine (48 mg) and tributylphosphine (40 mg) in tetrahydrofuran (2 mL) was stirred at room temperature for 15 hrs. After the completion of the reaction, water was added to the r... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | null | c1nc2c3c(cnn3CC[NH]2)n1 | c1ccccc1.c1ccccc1.c1nc2c3c(cnn3CC[NH]2)n1 | HO- | O1CCCC1.C(C)(=O)OCC | null | null | OCCn1ncc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21>O1CCCC1.C(C)(=O)OCC>Fc1cccc(COc2ccc(N3CCn4ncc5ncnc3c54)cc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-034af754bf884d1ea12687b62fb40f65 | CS(=O)(=O)CCNS(=O)(=O)c1ccccc1[N+](=O)[O-].OCCCn1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1>>CS(=O)(=O)CCN(CCCn1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1)S(=O)(=O)c1ccccc1[N+](=O)[O-] | ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C=2C(N=CN1)=CN(N2)CCCO.CS(=O)(=O)CCNS(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-].N(=NC(=O)N1CCCCC1)C(=O)N1CCCCC1.C(CCC)P(CCCC)CCCC>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C=2C(N=CN1)=CN(N2)CCCN(S(=O)(=O)C2=C(C=CC=C2)[N+](=O)[O-])CCS(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][NH:7][S:37](=[O:38])(=[O:39])[c:40]1[cH:41][cH:42][cH:43][cH:44][c:45]1[N+:46](=[O:47])[O-:48].O[CH2:8][CH2:9][CH2:10][n:11]1[cH:12][c:13]2[n:14][cH:15][n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]4[cH:26][cH:27][cH:28][c:29]([F:30])[cH:31]4)[c:32]([Cl:3... | CS(=O)(=O)CCNS(=O)(=O)c1ccccc1[N+](=O)[O-].OCCCn1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1 | CS(=O)(=O)CCN(CCCn1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1)S(=O)(=O)c1ccccc1[N+](=O)[O-] | null | null | O1CCCC1.O.C(C)(=O)OCC | Functional Group Addition | Mitsunobu_sulfonamide | 9f23fd0c198acf8676d599321e8bd3bc28283571d8896956098c9bfba87424c4 | dd6960be42016451db53d4bb29eae304cba1537cb8c971a9d4029dbee0005fed | O=S(=O)(NCCCn1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2n1)c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10] | null | [] | null | null | null | null | A solution of 3-[7-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-2H-pyrazolo[4,3-d]pyrimidin-2-yl]propanol (50 mg), N-[2-(methylsulfonyl)ethyl]-2-nitrobenzenesulfonamide (47 mg), 1,1′-(azodicarbonyl)dipiperidine (59 mg) and tributylphosphine (47 mg) in tetrahydrofuran (2 mL) was stirred at room temperature for 4 hrs.... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary alcohol | Tertiary amine | null | null | c1ncnc2c[nH]nc12.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1.O.C(C)(=O)OCC | null | null | CS(=O)(=O)CCNS(=O)(=O)c1ccccc1[N+](=O)[O-].OCCCn1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1>O1CCCC1.O.C(C)(=O)OCC>CS(=O)(=O)CCN(CCCn1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1)S(=O)(=O)c1ccccc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0cf50d1e7ae14f2abd7416ec81275647 | O=C(OCCOCCO)c1ccccc1.O=C1CCC(=O)N1I>>O=C(OCCOCCI)c1ccccc1 | C(O)([O-])=O.[Na+].C(C1=CC=CC=C1)(=O)OCCOCCO.IN1C(CCC1=O)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C1=CC=CC=C1)(=O)OCCOCCI | O[CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][C:2](=[O:1])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.O=C1CCC(=O)N1[I:9]>>[O:1]=[C:2]([O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][I:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | O=C(OCCOCCO)c1ccccc1.O=C1CCC(=O)N1I | O=C(OCCOCCI)c1ccccc1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:4]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:4] | 64.1 | [{"value": 64.1, "product": "C(C1=CC=CC=C1)(=O)OCCOCCI", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 2,2′-oxydiethanol (2.12 g) in pyridine (20 mL) was added benzoic anhydride (4.52 g) by small portions under ice-cooling, and the reaction mixture was stirred while warming to room temperature for 18 hrs. Pyridine was evaporated under reduced pressure and the obtained residue was diluted with diethyl et... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | ClCCl | null | 14 | O=C(OCCOCCO)c1ccccc1.O=C1CCC(=O)N1I>ClCCl>O=C(OCCOCCI)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e82edd567a44bb9a159177efafbc67a | Clc1ncnc2cc[nH]c12.O=C(OCCOCCI)c1ccccc1>>O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1 | C(O)([O-])=O.[Na+].C([O-])([O-])=O.[Cs+].[Cs+].ClC=1C2=C(N=CN1)C=CN2.C(C1=CC=CC=C1)(=O)OCCOCCI>>C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)Cl | [nH:9]1[cH:10][cH:11][c:12]2[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]12.I[CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][C:2](=[O:1])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[O:1]=[C:2]([O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][n:9]1[cH:10][cH:11][c:12]2[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]12)[c:19]1[cH:20][cH:21][cH:22][cH:... | Clc1ncnc2cc[nH]c12.O=C(OCCOCCI)c1ccccc1 | O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C(OCCOCCn1ccc2ncncc21)c1ccccc1 | I-[CH2;D2;+0:1]-[C:2]-[#8:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5](-[Cl;D1;H0:4]):[c:13]:2:1 | 55.4 | [{"value": 55.4, "product": "C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (0.659 g) in N,N-dimethylformamide (5.0 mL) was added cesium carbonate (3.13 g) under ice-cooling, and the reaction mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 2-(2-iodoethoxy)ethyl benzoate (1.45 g) prepared... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1 | HI | CN(C=O)C | null | null | Clc1ncnc2cc[nH]c12.O=C(OCCOCCI)c1ccccc1>CN(C=O)C>O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa93349175704aa0b74322613ac8dc75 | Nc1ccc(OCc2cccc(F)c2)c(Cl)c1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1>>O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21)c1ccccc1 | C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)Cl.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OCC2=CC(=CC=C2)F)Cl | [NH2:17][c:18]1[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]2)[c:31]([Cl:32])[cH:33]1.Cl[c:16]1[n:15][cH:14][n:13][c:12]2[cH:11][cH:10][n:9]([CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][C:2](=[O:1])[c:35]3[cH:36][cH:37][cH:38][cH:39][cH:40]3)[c:34]21>>[O:1]=[C:2]([O:3][CH2:4][CH2:5][O:6... | Nc1ccc(OCc2cccc(F)c2)c(Cl)c1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1 | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21)c1ccccc1 | null | null | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c21)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 87.7 | [{"value": 87.7, "product": "C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OCC2=CC(=CC=C2)F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | To a solution of 2-[2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy]ethyl benzoate (802 mg) in 1-methyl-2-pyrrolidone (8.0 mL) was added 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (745 mg), and the mixture was stirred in an oil bath at a temperature of 100° C. for 2 hrs. The reaction mixture was allowed to cool to room... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(O)([O-])=O.[Na+].CN1C(CCC1)=O | 100 | 2 | Nc1ccc(OCc2cccc(F)c2)c(Cl)c1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1>C(O)([O-])=O.[Na+].CN1C(CCC1)=O>O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5dd3a233d0b0418da20a7b2725f97734 | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21)c1ccccc1>>OCCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | Cl.C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OCC2=CC(=CC=C2)F)Cl.[OH-].[Na+]>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCOCCO | O=C(c1ccccc1)[O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]4[cH:23][cH:24][cH:25][c:26]([F:27])[cH:28]4)[c:29]([Cl:30])[cH:31]3)[c:32]12>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][... | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21)c1ccccc1 | OCCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | null | null | O1CCCC1 | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 8df1b5c4ec88eb8f4e334a9ade2ac7fc0b3f460ea1450816d1758f28eee39662 | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O=C(-[O;H0;D2;+0:1]-[C:2]-[C:3])-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[OH;D1;+0:1] | 69.6 | [{"value": 69.6, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 2-{2-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethoxy}ethyl benzoate (760 mg) in tetrahydrofuran (7.0 mL) was added 1N aqueous sodium hydroxide solution (7.0 mL), and the mixture was stirred at room temperature for 14 hrs. 1N Hydrochloric acid (7.0 mL) was added... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | c1ccccc1 | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | 14 | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21)c1ccccc1>O1CCCC1>OCCOCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb2a9f88bfa54bb89323fc87d4e34de6 | CC(=O)OCCCCBr.Clc1ncnc2cc[nH]c12>>CC(=O)OCCCCn1ccc2ncnc(Cl)c21 | C(O)([O-])=O.[Na+].C([O-])([O-])=O.[Cs+].[Cs+].ClC=1C2=C(N=CN1)C=CN2.C(C)(=O)OCCCCBr>>C(C)(=O)OCCCCN1C=CC=2N=CN=C(C21)Cl | Br[CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:2]([CH3:1])=[O:3].[nH:9]1[cH:10][cH:11][c:12]2[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]12>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH2:7][CH2:8][n:9]1[cH:10][cH:11][c:12]2[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]12 | CC(=O)OCCCCBr.Clc1ncnc2cc[nH]c12 | CC(=O)OCCCCn1ccc2ncnc(Cl)c21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5](-[Cl;D1;H0:4]):[c:13]:2:1 | 81 | [{"value": 81.0, "product": "C(C)(=O)OCCCCN1C=CC=2N=CN=C(C21)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (0.768 g) in N,N-dimethylformamide (10 mL) was added cesium carbonate (2.01 g) under ice-cooling, and the reaction mixture was stirred while warming to room temperature for 15 min. 4-Bromobutyl acetate (1.26 g) was added dropwise to the reaction mixture, and the m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HBr | CN(C=O)C | null | null | CC(=O)OCCCCBr.Clc1ncnc2cc[nH]c12>CN(C=O)C>CC(=O)OCCCCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5841be3715564e3c858c40ee32352d3c | CC(=O)OCCCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>>CC(=O)OCCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | C(O)([O-])=O.[Na+].C(C)(=O)OCCCCN1C=CC=2N=CN=C(C21)Cl.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)C(F)(F)F>>C(C)(=O)OCCCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl | Cl[c:16]1[n:15][cH:14][n:13][c:12]2[cH:11][cH:10][n:9]([CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:2]([CH3:1])=[O:3])[c:36]21.[NH2:17][c:18]1[cH:19][cH:20][c:21]([O:22][c:23]2[cH:24][cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]2)[c:33]([Cl:34])[cH:35]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH2:7][CH2:8][n:9]1[cH... | CC(=O)OCCCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1 | CC(=O)OCCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 50.1 | [{"value": 50.1, "product": "C(C)(=O)OCCCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3.5 | HOUR | To a solution of 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)butyl acetate (302 mg) in isopropyl alcohol (2.24 mL) was added 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (421 mg), and the mixture was stirred in an oil bath at a temperature of 100° C. for 3.5 hrs. The reaction mixture was allowed to cool to room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(C)(C)O | 100 | 3.5 | CC(=O)OCCCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>C(C)(C)O>CC(=O)OCCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66754c0c3895474cb1793a781c459cf7 | CC(=O)OCCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>OCCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | O.Cl.C(C)(=O)OCCCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl.[OH-].[Na+]>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCCCO | CC(=O)[O:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]([O:19][c:20]4[cH:21][cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29]4)[c:30]([Cl:31])[cH:32]3)[c:33]12>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]... | CC(=O)OCCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | OCCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O1CCCC1 | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 82.9 | [{"value": 82.9, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4.5 | HOUR | To a solution of 4-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]butyl acetate (281 mg) in tetrahydrofuran (4.0 mL) was added 1N aqueous sodium hydroxide solution (2.8 mL), and the mixture was stirred at room temperature for 4.5 hrs. 1N Aqueous hydrochloric acid solution (2.8... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | 4.5 | CC(=O)OCCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>O1CCCC1>OCCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-773dab546a1b4512929373d9e453fda4 | Clc1ncnc2cc[nH]c12.O=C(OCCI)c1ccccc1>>O=C(OCCn1ccc2ncnc(Cl)c21)c1ccccc1 | C(O)([O-])=O.[Na+].C([O-])([O-])=O.[Cs+].[Cs+].ClC=1C2=C(N=CN1)C=CN2.C(C1=CC=CC=C1)(=O)OCCI>>C(C1=CC=CC=C1)(=O)OCCN1C=CC=2N=CN=C(C21)Cl | [nH:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([Cl:14])[c:15]12.I[CH2:5][CH2:4][O:3][C:2](=[O:1])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[C:2]([O:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([Cl:14])[c:15]12)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | Clc1ncnc2cc[nH]c12.O=C(OCCI)c1ccccc1 | O=C(OCCn1ccc2ncnc(Cl)c21)c1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C(OCCn1ccc2ncncc21)c1ccccc1 | I-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]=[O;D1;H0:5].[Cl;D1;H0:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[c:13]:[nH;D2;+0:14]:[c:15]:1:2>>[Cl;D1;H0:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[c:13]:[n;H0;D3;+0:14](-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]=[O;D1;H0:5]):[c:15]:1:2 | 74 | [{"value": 74.0, "product": "C(C1=CC=CC=C1)(=O)OCCN1C=CC=2N=CN=C(C21)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (141 mg) in N,N-dimethylformamide (2.5 mL) was added cesium carbonate (358 mg) under ice-cooling, and the reaction mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 2-iodoethyl benzoate (298 mg), and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1 | HI | CN(C=O)C | null | null | Clc1ncnc2cc[nH]c12.O=C(OCCI)c1ccccc1>CN(C=O)C>O=C(OCCn1ccc2ncnc(Cl)c21)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f3987e234d94d20946c7cb74fdab4d9 | CCOC(=O)Cn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>CCOC(=O)Cn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | ClC=1C2=C(N=CN1)C=CN2CC(=O)OCC.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>C(C)OC(CN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OCC2=CC(=CC=C2)F)Cl)=O | Cl[c:14]1[n:13][cH:12][n:11][c:10]2[cH:9][cH:8][n:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:32]21.[NH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][c:26]([F:27])[cH:28]2)[c:29]([Cl:30])[cH:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][c:14]([N... | CCOC(=O)Cn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | CCOC(=O)Cn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | null | null | C(O)([O-])=O.[Na+].C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]-[C:10](-[#8:11])=[O;D1;H0:12]):[c:13]:2:1.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[#8:11]-[C:10](=[O;D1;H0:12])-[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17]):[c:13]:1:2 | 73.9 | [{"value": 73.9, "product": "C(C)OC(CN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OCC2=CC(=CC=C2)F)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2.5 | HOUR | To a solution of ethyl (4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)acetate (530 mg) in isopropyl alcohol (4.0 mL) was added 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (695 mg), and the mixture was stirred in an oil bath at a temperature of 100° C. for 2.5 hrs. The reaction mixture was allowed to cool to room temperature, di... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(O)([O-])=O.[Na+].C(C)(C)O | 100 | 2.5 | CCOC(=O)Cn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>C(O)([O-])=O.[Na+].C(C)(C)O>CCOC(=O)Cn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-91aaa449c91348bb929eeb8cd389eff7 | Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1.O=C(O)Cn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21>>OCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CC(=O)O.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)C(F)(F)F.C(C)(C)O>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCCO | [NH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][c:19]2[cH:20][cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28]2)[c:29]([Cl:30])[cH:31]1.O=[C:3]([OH:1])[CH2:4][n:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11][c:12](Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)[c:32]12>>[OH:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11][c... | Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1.O=C(O)Cn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | OCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(O)([O-])=O.[Na+] | Heteroatom Alkylation and Arylation | OtherReaction | fdeeff255473a8260f54263d9096a7f76e7ac18cb09daa2dec4e9f123a666948 | abc5084dea55c1964dd3357214e394c9a903fafb1790a10c5463f3ddcad62abf | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-c1:c:c(-N-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]3:[c:6]:[c:7]:[#7;a:8](-[C:9]-[C;H0;D3;+0:10](=O)-[OH;D1;+0:11]):[c:12]:3:2):c:c:c:1-O-C-c1:c:c:c:c(-F):c:1.[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16]>>[OH;D1;+0:11]-[C:17]-[CH2;D2;+0:10]-[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;... | null | [] | 100 | CELSIUS | 2 | HOUR | To a solution of 3-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)propan-1-ol (201 mg) synthesized in Example 53 (ii) in isopropyl alcohol (2.5 mL) was added 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (381 mg), and the mixture was stirred in an oil bath at a temperature of 100° C. for 2.0 hrs. The reaction mixture was a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Ether.Primary amine.Secondary amine | Primary alcohol.Secondary amine | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HF | C(O)([O-])=O.[Na+] | 100 | 2 | Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1.O=C(O)Cn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21>C(O)([O-])=O.[Na+]>OCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e98eabfe0b5476ea944c55d3bf91415 | O=C=NC(=O)C(Cl)(Cl)Cl.OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>NC(=O)OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | C(O)([O-])=O.[Na+].ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCCO.ClC(C(=O)N=C=O)(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>>C(N)(OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl)=O | O=C(C(Cl)(Cl)Cl)[N:1]=[C:2]=[O:3].[OH:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][n:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]([O:23][c:24]4[cH:25][cH:26][cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33]4)[c:34]([Cl:35])[cH:36]3)[c:37]12>>[NH2:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][O:7][... | O=C=NC(=O)C(Cl)(Cl)Cl.OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | NC(=O)OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | CO.C(C)(=O)OCC.O1CCCC1 | Functional Group Interconversion | OtherReaction | 33f87a7eae2df2a7210c594ad669288679a7cd9748993148364fdbfb809c16e1 | 3b98ea8a78a0abdc8cc7b55549f4de65599a6b8f023ee5f306970eb36ff4bd74 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-C(-Cl)(-Cl)-C(=O)-[N;H0;D2;+0:1]=[C;H0;D2;+0:2]=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:2](-[NH2;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | 3 | HOUR | To a solution of 2-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethoxy}ethanol (84 mg) in a mixed solvent (1.0 mL) of toluene/dichloromethane (1/1) was added trichloroacetyl isocyanate (22 μL) under ice-cooling, and the mixture was stirred for 3 hrs. To the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Isocyanate.Primary alcohol | Carbamic ester | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | Other | CO.C(C)(=O)OCC.O1CCCC1 | null | 3 | O=C=NC(=O)C(Cl)(Cl)Cl.OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>CO.C(C)(=O)OCC.O1CCCC1>NC(=O)OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69a0d92cc2b54fabb3d39c9797b6bd22 | Nc1ccc(Oc2cccc(Cl)c2)c(Cl)c1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1>>OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 | C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)Cl.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)Cl.CN1C(CCC1)=O.C(O)([O-])=O.[Na+]>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)Cl)NC=1C2=C(N=CN1)C=CN2CCOCCO | [NH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[cH:27]2)[c:28]([Cl:29])[cH:30]1.O=C(c1ccccc1)[O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][c:14](Cl)[c:31]12>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][c:1... | Nc1ccc(Oc2cccc(Cl)c2)c(Cl)c1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1 | OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | e83d3b14c87cd29b2801fdf995368b0a2da0018f312296eb02835cf026e36ef5 | 03164802232677317a7efd0e24d53056dbf9714f8e35a1ee2da95661003b43d6 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.O=C(-[O;H0;D2;+0:11]-[C:12]-[C:13])-c1:c:c:c:c:c:1.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17]):[c:10]:1:2.[C:13]-[C:12]-[O... | 67.9 | [{"value": 67.9, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)Cl)NC=1C2=C(N=CN1)C=CN2CCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 2 | HOUR | A mixture of 2-[2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy]ethyl benzoate (346 mg), 3-chloro-4-(3-chlorophenoxy)aniline (280 mg) and 1-methyl-2-pyrrolidone (3 mL) was stirred at 120° C. for 2 hrs. Water and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture and the mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Primary alcohol.Secondary amine | c1ccccc1.c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | O | 120 | 2 | Nc1ccc(Oc2cccc(Cl)c2)c(Cl)c1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1>O>OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4bcf95170ce4ab1a0e5e7f5db86573a | Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1>>OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)Cl.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)C(F)(F)F.CN1C(CCC1)=O.C(O)([O-])=O.[Na+]>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCCO | [NH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]2)[c:31]([Cl:32])[cH:33]1.O=C(c1ccccc1)[O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][c:14](Cl)[c:34]12>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][n:7]1[cH:8][cH:9][c:10]2[n... | Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1 | OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | e83d3b14c87cd29b2801fdf995368b0a2da0018f312296eb02835cf026e36ef5 | 03164802232677317a7efd0e24d53056dbf9714f8e35a1ee2da95661003b43d6 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.O=C(-[O;H0;D2;+0:11]-[C:12]-[C:13])-c1:c:c:c:c:c:1.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17]):[c:10]:1:2.[C:13]-[C:12]-[O... | 63.1 | [{"value": 63.1, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 1.5 | HOUR | A mixture of 2-[2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy]ethyl benzoate (1.037 g), 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (863 mg) and 1-methyl-2-pyrrolidone (10 mL) was stirred at 120° C. for 1.5 hrs. Water and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Primary alcohol.Secondary amine | c1ccccc1.c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | O | 120 | 1.5 | Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1>O>OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa870444d32142039569b5b9aaf814bf | CC(=O)c1cccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)c1>>CC(O)c1cccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)c1 | O.ClC1=C(OC=2C=C(C=CC2)C(C)=O)C=CC(=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO.[BH4-].[Na+]>>ClC1=C(OC=2C=C(C=CC2)C(C)O)C=CC(=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][c:13]([NH:14][c:15]3[n:16][cH:17][n:18][c:19]4[cH:20][cH:21][n:22]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][OH:28])[c:29]34)[cH:30][c:31]2[Cl:32])[cH:33]1>>[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][c:13]([NH:1... | CC(=O)c1cccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)c1 | CC(O)c1cccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)c1 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6] | 96.2 | [{"value": 96.2, "product": "ClC1=C(OC=2C=C(C=CC2)C(C)O)C=CC(=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 1-{3-[2-chloro-4-({5-[2-(2-hydroxyethoxy)ethyl]-5H-pyrrolo[3,2-d]pyrimidin-4-yl}amino)phenoxy]phenyl}ethanone (233 mg) in methanol (5 mL) was added sodium borohydride (38 mg), and the mixture was stirred at room temperature for 2 hrs. Water was added to the reaction mixture and the mixture was extracte... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.c1ccccc1.c1ncnc2cc[nH]c12 | null | CO | null | 2 | CC(=O)c1cccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)c1>CO>CC(O)c1cccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d88a4a67db144f34b7f3c8dad50b4257 | CC(=O)OCCCCCBr.Clc1ncnc2cc[nH]c12>>CC(=O)OCCCCCn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.C(C)(=O)OCCCCCBr.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>>C(C)(=O)OCCCCCN1C=CC=2N=CN=C(C21)Cl | Br[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:2]([CH3:1])=[O:3].[nH:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][n:16][c:17]([Cl:18])[c:19]12>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][n:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][n:16][c:17]([Cl:18])[c:19]12 | CC(=O)OCCCCCBr.Clc1ncnc2cc[nH]c12 | CC(=O)OCCCCCn1ccc2ncnc(Cl)c21 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5](-[Cl;D1;H0:4]):[c:13]:2:1 | null | [] | 40 | CELSIUS | 4 | DAY | A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (0.50 g), 5-bromopentyl acetate (0.71 mL), cesium carbonate (1.59 g) and N,N-dimethylformamide (5.0 mL) was stirred at 40° C. for 4 days. Water was added to the reaction system and the mixture was extracted with ethyl acetate. The organic layer washed with water and sat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HBr | O | 40 | 96 | CC(=O)OCCCCCBr.Clc1ncnc2cc[nH]c12>O>CC(=O)OCCCCCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a7a6ad084d14aa6a6a245b8957cd0b0 | CC(=O)OCCCCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>>OCCCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | Cl.C(C)(=O)OCCCCCN1C=CC=2N=CN=C(C21)Cl.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)C(F)(F)F.[OH-].[Na+]>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCCCCO | CC(=O)[O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][c:14](Cl)[c:34]12.[NH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]2)[c:31]([Cl:32])[cH:33]1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11... | CC(=O)OCCCCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1 | OCCCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 5fb054ac892ff957f786943c492739383043e2232d2e947412bf3bcb16a4d832 | 03164802232677317a7efd0e24d53056dbf9714f8e35a1ee2da95661003b43d6 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3].Cl-[c;H0;D3;+0:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]2:[c:9]:[c:10]:[#7;a:11](-[C:12]):[c:13]:2:1.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[C:12]-[#7;a:11]1:[c:10]:[c:9]:[c:8]2:[#7;a:7]:[c:6]:[#7;a:5]:[c;H0;D3;+0:4](-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17]):[c:13]:1:2.[C:3]-[C:2]-[OH;D1;+0:1] | 78.9 | [{"value": 78.9, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 5-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)pentyl acetate (200 mg) and 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (265 mg) in isopropyl alcohol (3.5 mL) was stirred at 80° C. for 14 hrs. 1N Aqueous sodium hydroxide solution (2.1 mL) was added at 0° C., and the mixture was stirred at room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Primary alcohol.Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(C)(C)O | null | 1 | CC(=O)OCCCCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>C(C)(C)O>OCCCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3cea77641f5649189d78454d611acd8f | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>>CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | C(C)(C)(C)OC(NCCN1C=CC=2N=CN=C(C21)Cl)=O.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)C(F)(F)F.C(O)([O-])=O.[Na+]>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O | Cl[c:18]1[n:17][cH:16][n:15][c:14]2[cH:13][cH:12][n:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:38]21.[NH2:19][c:20]1[cH:21][cH:22][c:23]([O:24][c:25]2[cH:26][cH:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34]2)[c:35]([Cl:36])[cH:37]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:... | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 85.2 | [{"value": 85.2, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of tert-butyl[2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethyl]carbamate (712 mg) and 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (830 mg) in isopropyl alcohol (7.1 mL) was stirred at 80° C. for 12 hrs. Aqueous sodium hydrogen carbonate was added to the reaction system and the mixture was extracted with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(C)(C)O | null | null | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>C(C)(C)O>CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0805037c033e42fbb8d182e21360be2e | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O.Cl>>Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl | CC(C)(C)OC(=O)[NH:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]([O:19][c:20]4[cH:21][cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29]4)[c:30]([Cl:2])[cH:32]3)[c:33]12>>[ClH:2].[NH2:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([NH:14][c:... | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O1CCCC1 | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | f9b0ddd5e086b40f0768881f9b226acdc5a9dc29f99a9283af567e925b55a3d7 | b15a28c2a3fd58b98c3a6c1b435f8c25519aeb02339cc9ac8ff8fecd35099d5c | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[Cl;H0;D1;+0:8]):[c:9]:[c:10]>>[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[Cl;D1;H0:11]):[c:9]:[c:10].[C:3]-[C:2]-[NH2;D1;+0:1].[ClH;D0;+0:8] | null | [] | 60 | CELSIUS | 20 | HOUR | A mixture of tert-butyl {2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}carbamate (1.12 g), 2N hydrochloric acid (15 mL) and tetrahydrofuran (30 mL) was stirred at 60° C. for 20 hrs. The solvent was evaporated under reduced pressure, ethanol was added, and the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boc | Aromatic halide.Primary amine | c1ccccc1 | c1ccccc1 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | 60 | 20 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>O1CCCC1>Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79c24a4ee86c4932967eeb4ae61c23e9 | NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.O=C(O)CO>>O=C(CO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl.C(CO)(=O)O.Cl.C(C)N=C=NCCCN(C)C.O.ON1N=NC2=C1C=CC=C2>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CO)=O | [NH2:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][c:20]([O:21][c:22]4[cH:23][cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31]4)[c:32]([Cl:33])[cH:34]3)[c:35]12.O[C:2](=[O:1])[CH2:3][OH:4]>>[O:1]=[C:2]([CH2:3][OH:4])[NH:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10][c:11]... | NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.O=C(O)CO | O=C(CO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O.C(C)N(CC)CC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[O;D1;H1:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[O;D1;H1:4] | 105.9 | [{"value": 105.9, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | A mixture of 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (105 mg), glycolic acid (44 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (167 mg), 1-hydroxybenzotriazole monohydrate (133 mg), triethylamine (0.40 mL) and N,N-dimethylf... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O.C(C)N(CC)CC.CN(C=O)C | null | 72 | NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.O=C(O)CO>O.C(C)N(CC)CC.CN(C=O)C>O=C(CO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-239c2610297a47f4a9d56c00dd658b66 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(OC(F)(F)F)c2)c(Cl)c1>>CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 | C(C)(C)(C)OC(NCCN1C=CC=2N=CN=C(C21)Cl)=O.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)OC(F)(F)F.C(O)([O-])=O.[Na+]>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)OC(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O | Cl[c:18]1[n:17][cH:16][n:15][c:14]2[cH:13][cH:12][n:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:39]21.[NH2:19][c:20]1[cH:21][cH:22][c:23]([O:24][c:25]2[cH:26][cH:27][cH:28][c:29]([O:30][C:31]([F:32])([F:33])[F:34])[cH:35]2)[c:36]([Cl:37])[cH:38]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6... | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(OC(F)(F)F)c2)c(Cl)c1 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 91 | [{"value": 91.0, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)OC(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of tert-butyl[2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethyl]carbamate (100 mg), 3-chloro-4-[3-(trifluoromethoxy)phenoxy]aniline (153 mg) in isopropyl alcohol (1.5 mL) was stirred at 80° C. for 12 hrs. Aqueous sodium hydrogen carbonate was added to the reaction system and the mixture was extracted with et... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(C)(C)O | null | null | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(OC(F)(F)F)c2)c(Cl)c1>C(C)(C)O>CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d8e188778803426b81d3af97cc979968 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21>>Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 | ClC=1C=C(C=CC1OC1=CC(=CC=C1)OC(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O.Cl.O1CCCC1>>Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)OC(F)(F)F)Cl | CC(C)(C)OC(=O)[NH:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]([O:19][c:20]4[cH:21][cH:22][cH:23][c:24]([O:25][C:26]([F:27])([F:28])[F:29])[cH:30]4)[c:31]([Cl:1])[cH:33]3)[c:34]12>>[ClH:1].[NH2:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([NH:... | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 | Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(C)O | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | f9b0ddd5e086b40f0768881f9b226acdc5a9dc29f99a9283af567e925b55a3d7 | b15a28c2a3fd58b98c3a6c1b435f8c25519aeb02339cc9ac8ff8fecd35099d5c | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[Cl;H0;D1;+0:8]):[c:9]:[c:10]>>[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[Cl;D1;H0:11]):[c:9]:[c:10].[C:3]-[C:2]-[NH2;D1;+0:1].[ClH;D0;+0:8] | null | [] | 60 | CELSIUS | 6 | HOUR | A mixture of tert-butyl {2-[4-({3-chloro-4-[3-(trifluoromethoxy)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}carbamate (173 mg), 2N hydrochloric acid (2.5 mL) and tetrahydrofuran (5.0 mL) was stirred at 60° C. for 6 hrs. Ethanol was added to the reaction system. The solvent was evaporated under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boc | Aromatic halide.Primary amine | c1ccccc1 | c1ccccc1 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | C(C)O | 60 | 6 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21>C(C)O>Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-204f4bc7c02942d999e1baa8bd69587e | CS(=O)(=O)CC(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21>>CS(=O)(=O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 | Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)OC(F)(F)F)Cl.CS(=O)(=O)CC(=O)O.Cl.C(C)N=C=NCCCN(C)C.O.ON1N=NC2=C1C=CC=C2>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)OC(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CS(=O)(=O)C)=O | O[C:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])=[O:7].[NH2:8][CH2:9][CH2:10][n:11]1[cH:12][cH:13][c:14]2[n:15][cH:16][n:17][c:18]([NH:19][c:20]3[cH:21][cH:22][c:23]([O:24][c:25]4[cH:26][cH:27][cH:28][c:29]([O:30][C:31]([F:32])([F:33])[F:34])[cH:35]4)[c:36]([Cl:37])[cH:38]3)[c:39]12>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][C:6]... | CS(=O)(=O)CC(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 | CS(=O)(=O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 | null | null | O.C(C)N(CC)CC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#16:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#16:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 64.3 | [{"value": 64.3, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)OC(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CS(=O)(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A mixture of 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethoxy)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (160 mg), 2-(methylsulfonyl)acetic acid (82.3 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (171 mg), 1-hydroxybenzotriazole monohydrate (137 mg), triethylamine (0.42 mL... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O.C(C)N(CC)CC.CN(C=O)C | null | 20 | CS(=O)(=O)CC(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21>O.C(C)N(CC)CC.CN(C=O)C>CS(=O)(=O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1df4735396ea4b2083cad97a8c0dd483 | CC(C)(O)CC(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CC(C)(O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl.OC(CC(=O)O)(C)C.Cl.C(C)N=C=NCCCN(C)C.O.ON1N=NC2=C1C=CC=C2>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CC(C)(C)O)=O | O[C:6]([CH2:5][C:2]([CH3:1])([CH3:3])[OH:4])=[O:7].[NH2:8][CH2:9][CH2:10][n:11]1[cH:12][cH:13][c:14]2[n:15][cH:16][n:17][c:18]([NH:19][c:20]3[cH:21][cH:22][c:23]([O:24][c:25]4[cH:26][cH:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34]4)[c:35]([Cl:36])[cH:37]3)[c:38]12>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][C:6](=[O... | CC(C)(O)CC(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CC(C)(O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O.C(C)N(CC)CC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 77.3 | [{"value": 77.3, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CC(C)(C)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | DAY | A mixture of 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (150 mg), 3-hydroxy-3-methylbutyric acid (68 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (166 mg), 1-hydroxybenzotriazole monohydrate (133 mg), triethylamine (0.40 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O.C(C)N(CC)CC.CN(C=O)C | null | 120 | CC(C)(O)CC(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>O.C(C)N(CC)CC.CN(C=O)C>CC(C)(O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-269849cb0438467bbc399959501fa623 | CC(=O)OC(C)(C)C(=O)Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CC(C)(O)C(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | C(O)([O-])=O.[Na+].Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl.C(C)N(CC)CC.C(C)(=O)OC(C)(C)C(=O)Cl>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(C(C)(C)O)=O | CC(=O)[O:4][C:2]([CH3:1])([CH3:3])[C:5](Cl)=[O:6].[NH2:7][CH2:8][CH2:9][n:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]([O:23][c:24]4[cH:25][cH:26][cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33]4)[c:34]([Cl:35])[cH:36]3)[c:37]12>>[CH3:1][C:2]([CH3:3])([OH:4])[C:5](=[O:6])[NH:7... | CC(=O)OC(C)(C)C(=O)Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CC(C)(O)C(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O1CCCC1 | Acylation | OtherReaction | 8f4d393863b330ba0cd4643324ec7f42b8a96377d9661c45bd7200fb61005bfa | cdefc707d63bca19b5324fc80744fd8bf75a451b88388829a5e6313422373323 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;H0;D3;+0:5](-Cl)=[O;D1;H0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[OH;D1;+0:1] | null | [] | null | null | 3 | DAY | To a suspension of 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (150 mg) and triethylamine (0.40 mL) in tetrahydrofuran (5.0 mL) was added 1-chlorocarbonyl-1-methylethyl acetate (0.12 mL) at room temperature. After stirring at room temperature for... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Primary amine | Secondary amide.Tertiary alcohol | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | O1CCCC1 | null | 72 | CC(=O)OC(C)(C)C(=O)Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>O1CCCC1>CC(C)(O)C(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5b3ff5a9c924e8dabf2513ecfbb0819 | CS(=O)(=O)CC(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CS(=O)(=O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl.CS(=O)(=O)CC(=O)O.Cl.C(C)N=C=NCCCN(C)C.O.ON1N=NC2=C1C=CC=C2>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CS(=O)(=O)C)=O | O[C:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])=[O:7].[NH2:8][CH2:9][CH2:10][n:11]1[cH:12][cH:13][c:14]2[n:15][cH:16][n:17][c:18]([NH:19][c:20]3[cH:21][cH:22][c:23]([O:24][c:25]4[cH:26][cH:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34]4)[c:35]([Cl:36])[cH:37]3)[c:38]12>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][C:6](=[O:7... | CS(=O)(=O)CC(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CS(=O)(=O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O.C(C)N(CC)CC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#16:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#16:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 78.2 | [{"value": 78.2, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CS(=O)(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A mixture of 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (150 mg), 2-(methylsulfonyl)acetic acid (79.6 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (166 mg), 1-hydroxybenzotriazole monohydrate (133 mg), triethylamine (0.40 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O.C(C)N(CC)CC.CN(C=O)C | null | 20 | CS(=O)(=O)CC(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>O.C(C)N(CC)CC.CN(C=O)C>CS(=O)(=O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8edad025422d40d3969bed25859bb17d | BrC(Br)(Br)Br.CC(O)(CCO)CCOC(=O)c1ccccc1>>CC(O)(CCBr)CCOC(=O)c1ccccc1 | O.C(C1=CC=CC=C1)(=O)OCCC(CCO)(C)O.C(Br)(Br)(Br)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C1=CC=CC=C1)(=O)OCCC(CCBr)(C)O | BrC(Br)(Br)[Br:6].O[CH2:5][CH2:4][C:2]([CH3:1])([OH:3])[CH2:7][CH2:8][O:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][C:2]([OH:3])([CH2:4][CH2:5][Br:6])[CH2:7][CH2:8][O:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | BrC(Br)(Br)Br.CC(O)(CCO)CCOC(=O)c1ccccc1 | CC(O)(CCBr)CCOC(=O)c1ccccc1 | null | null | O1CCCC1 | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccccc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4] | 77.5 | [{"value": 77.5, "product": "C(C1=CC=CC=C1)(=O)OCCC(CCBr)(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a solution of 3,5-dihydroxy-3-methylpentyl benzoate (1.0 g) and carbon tetrabromide (2.78 g) in tetrahydrofuran (30 mL) was added dropwise a solution of triphenylphosphine (2.20 g) in tetrahydrofuran (10 mL) under ice-cooling. After stirring at room temperature for 3 days, water was added, and the mixture was extrac... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccccc1 | HBr | O1CCCC1 | null | 72 | BrC(Br)(Br)Br.CC(O)(CCO)CCOC(=O)c1ccccc1>O1CCCC1>CC(O)(CCBr)CCOC(=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77393fc65ff34169adaaff01e832835b | O=C(OCCI)c1ccccc1.OCCS>>O=C(OCCSCCO)c1ccccc1 | O.SCCO.C(C1=CC=CC=C1)(=O)OCCI.C(C)N(C(C)C)C(C)C>>C(C1=CC=CC=C1)(=O)OCCSCCO | I[CH2:5][CH2:4][O:3][C:2](=[O:1])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[SH:6][CH2:7][CH2:8][OH:9]>>[O:1]=[C:2]([O:3][CH2:4][CH2:5][S:6][CH2:7][CH2:8][OH:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | O=C(OCCI)c1ccccc1.OCCS | O=C(OCCSCCO)c1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 77cd742b5ba20df0e225494f6e5f3d958ee82ce9a1b16fd99a2d9f8350b4fdc8 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | c1ccccc1 | I-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]=[O;D1;H0:5].[C:6]-[C:7]-[SH;D1;+0:8]>>[C:6]-[C:7]-[S;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]=[O;D1;H0:5] | null | [] | null | null | null | null | A solution of 2-mercaptoethanol (1.52 mL), 2-iodoethyl benzoate (6.00 g) and ethyldiisopropylamine (4.53 mL) in N,N-dimethylformamide (60 mL) was stirred at 40° C. for 3 days. Water was added to the reaction system and the mixture was extracted with ethyl acetate. The organic layer washed with saturated brine, dried ov... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | null | null | c1ccccc1 | HI | CN(C=O)C | null | null | O=C(OCCI)c1ccccc1.OCCS>CN(C=O)C>O=C(OCCSCCO)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7bf0f327fdc04e4c84fb4419c62b0309 | OCCSCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>O=S(CCO)CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | S(=S)(=O)([O-])[O-].[Na+].[Na+].ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCSCCO.ClC1=CC(=CC=C1)C(=O)OO>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCS(=O)CCO | [S:2]([CH2:3][CH2:4][OH:5])[CH2:6][CH2:7][n:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][c:20]([O:21][c:22]4[cH:23][cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31]4)[c:32]([Cl:33])[cH:34]3)[c:35]12>>[O:1]=[S:2]([CH2:3][CH2:4][OH:5])[CH2:6][CH2:7][n:8]1[cH:9][cH:10][c:11]2[n:12]... | OCCSCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | O=S(CCO)CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | ClCCl | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[C:4]-[C:5]>>[C:1]-[C:2]-[S;H0;D3;+0:3](=[O;D1;H0:6])-[C:4]-[C:5] | 84.3 | [{"value": 84.3, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCS(=O)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | To a solution of 2-({2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}thio)ethanol (100 mg) in dichloromethane (10 mL) was added dropwise a 70% solution of 3-chloroperbenzoic acid (58 mg) in dichloromethane (5.0 mL) at −78° C. The mixture was stirred at −78° C. for 1 hr,... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | null | ClCCl | -78 | 1 | OCCSCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>ClCCl>O=S(CCO)CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-93b81ce4bf3941fea8de99cbba19a7da | CC(C)(C)OO.OCCSCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>O=S(=O)(CCO)CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | S(=S)(=O)([O-])[O-].[Na+].[Na+].ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCSCCO.CO.C(C)(C)(C)OO>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCS(=O)(=O)CCO | CC(C)(C)O[OH:1].[S:2]([CH2:4][CH2:5][OH:6])[CH2:7][CH2:8][n:9]1[cH:10][cH:11][c:12]2[n:13][cH:14][n:15][c:16]([NH:17][c:18]3[cH:19][cH:20][c:21]([O:22][c:23]4[cH:24][cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]4)[c:33]([Cl:34])[cH:35]3)[c:36]12>>[O:1]=[S:2](=[O:3])([CH2:4][CH2:5][OH:6])[CH2:7][CH2:8][n:9]1[... | CC(C)(C)OO.OCCSCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | O=S(=O)(CCO)CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4] | ClCCl.O | Oxidation | OtherReaction | 73ca5438c687e7554e6372a79a1d180e809287a4397486487708df09a5fd20e0 | ebe5803abbd530cb5af8bdb9d457c04c55bf786787bd2848bd344ab633fecdcb | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-O-[OH;D1;+0:1].[C:2]-[C:3]-[S;H0;D2;+0:4]-[C:5]-[C:6]>>[C:2]-[C:3]-[S;H0;D4;+0:4](=[O;D1;H0:7])(=[O;H0;D1;+0:1])-[C:5]-[C:6] | null | [] | null | null | 2 | DAY | A solution of 2-({2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}thio)ethanol (150 mg), titanium tetraisopropoxide (43 μL), methanol (24 μL) and water (10 μL) in dichloromethane was stirred at room temperature for 30 min. 70% Aqueous tert-butyl hydroperoxide solution (... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Monosulfide | Sulfone | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].ClCCl.O | null | 48 | CC(C)(C)OO.OCCSCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].ClCCl.O>O=S(=O)(CCO)CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a7652cbac98d4c6f9402b793e9335258 | CS(=O)(=O)CC(=O)NCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21.NCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21>>CS(=O)(=O)CC(=O)NCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 | ClC=1C=C(C=CC1OC1=CC(=CC=C1)OC(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCCNC(CS(=O)(=O)C)=O.Cl.C(C)N=C=NCCCN(C)C.Cl.Cl.NCCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)OC(F)(F)F)Cl.CS(=O)(=O)CC(=O)O.O.ON1N=NC2=C1C=CC=C2.ClC=1C=C(C=CC1OC1=CC(=CC=C1)OC(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCCNC(CS(=O)(=O)C)=O.Cl.C(C)(=O)OCC>>Cl.ClC=1C=C(C=C... | FC(F)(F)Oc1cccc(Oc2ccc(Nc3ncnc4ccn(CCCN[C:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])=[O:7])c34)cc2Cl)c1.[NH2:8][CH2:9][CH2:10][CH2:11][n:12]1[cH:13][cH:14][c:15]2[n:16][cH:17][n:18][c:19]([NH:20][c:21]3[cH:22][cH:23][c:24]([O:25][c:26]4[cH:27][cH:28][cH:29][c:30]([O:31][C:32]([F:33])([F:34])[F:35])[cH:36]4)[c:37]([Cl:38])... | CS(=O)(=O)CC(=O)NCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21.NCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 | CS(=O)(=O)CC(=O)NCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | Acylation | OtherReaction | 9a80cb011345d53a753f70410463fab736528323482f3a109b1e5714cb11ae66 | 6db9e17a32e5d748d0a5cb84cbaf34f02d84fa7a1be4d349503805b53101cee5 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-c1:c:c(-N-c2:n:c:n:c3:c:c:n(-C-C-C-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#16:4]):c:2:3):c:c:c:1-O-c1:c:c:c:c(-O-C(-F)(-F)-F):c:1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[#16:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | 1 | HOUR | N-{3-[4-({3-Chloro-4-[3-(trifluoromethoxy)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]propyl}-2-(methylsulfonyl)acetamide was obtained by the reaction in the same manner as in Example 155 (iv) using 5-(3-aminopropyl)-N-{3-chloro-4-[3-(trifluoromethoxy)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydro... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Ether.Ether.Secondary amide.Primary amine.Secondary amine | Secondary amide | c1ccccc1.c1ccccc1.c1ncc2[nH]ccc2n1 | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HF | C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | null | 1 | CS(=O)(=O)CC(=O)NCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21.NCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21>C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC>CS(=O)(=O)CC(=O)NCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-602a1e59608c4dbda81676c59b415328 | CSCCC(=O)Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CSCCC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | O.Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl.C(C)N(CC)CC.CSCCC(=O)Cl>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CCSC)=O | Cl[C:5]([CH2:4][CH2:3][S:2][CH3:1])=[O:6].[NH2:7][CH2:8][CH2:9][n:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]([O:23][c:24]4[cH:25][cH:26][cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33]4)[c:34]([Cl:35])[cH:36]3)[c:37]12>>[CH3:1][S:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][CH2:8][CH... | CSCCC(=O)Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CSCCC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | 20 | HOUR | To a mixture of 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (230 mg) and triethylamine (0.61 mL) in tetrahydrofuran (8.0 mL) was added 3-(methylthio)propionyl chloride (0.15 mL) under ice-cooling. After stirring at room temperature for 20 hrs, wa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | O1CCCC1 | null | 20 | CSCCC(=O)Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>O1CCCC1>CSCCC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff13d238df324253886e7c569ec3cabb | CS(=O)(=O)Cl.OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CSCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | C(O)([O-])=O.[Na+].C(C)N(CC)CC.CS(=O)(=O)Cl.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCCO>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCCSC | O=[S:2](=O)(Cl)[CH3:1].O[CH2:3][CH2:4][O:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][c:20]([O:21][c:22]4[cH:23][cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31]4)[c:32]([Cl:33])[cH:34]3)[c:35]12>>[CH3:1][S:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][n:8]1[cH:9][cH:10... | CS(=O)(=O)Cl.OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CSCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 108da928d521d41c3da319e77a1c3806ba2927ec9c57394164d583393bb9f6b8 | 1b8de9fa8b21bb7b8a61939a186399cd62ad0963c1e300c43d1add619b5fc816 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[S;H0;D4;+0:1](=O)(=O)-[C;D1;H3:2].O-[CH2;D2;+0:3]-[C:4]-[#8:5]>>[#8:5]-[C:4]-[CH2;D2;+0:3]-[S;H0;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | 1 | HOUR | The compound (150 mg) of Example 147 was dissolved in tetrahydrofuran (10 mL) and triethylamine (1.50 mL) and methanesulfonyl chloride (0.70 mL) were added under ice-cooling, and the mixture was stirred for 1 hr. Saturated aqueous sodium hydrogen carbonate was added to this reaction solution under ice-cooling, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Monosulfide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | O1CCCC1 | null | 1 | CS(=O)(=O)Cl.OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>O1CCCC1>CSCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dacf341508f24341899bb9c208a16e3c | CC(C)(C)OO.CSCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CS(=O)(=O)CCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | S(=S)(=O)([O-])[O-].[Na+].[Na+].CO.C(C)(C)(C)OO.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCCSC>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCCS(=O)(=O)C | CC(C)(C)O[OH:4].[CH3:1][S:2][CH2:5][CH2:6][O:7][CH2:8][CH2:9][n:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]([O:23][c:24]4[cH:25][cH:26][cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33]4)[c:34]([Cl:35])[cH:36]3)[c:37]12>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][O:7][CH2:8][CH... | CC(C)(C)OO.CSCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CS(=O)(=O)CCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4] | ClCCl | Oxidation | OtherReaction | 73ca5438c687e7554e6372a79a1d180e809287a4397486487708df09a5fd20e0 | ebe5803abbd530cb5af8bdb9d457c04c55bf786787bd2848bd344ab633fecdcb | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-O-[OH;D1;+0:1].[C:2]-[C:3]-[S;H0;D2;+0:4]-[C;D1;H3:5]>>[C:2]-[C:3]-[S;H0;D4;+0:4](-[C;D1;H3:5])(=[O;D1;H0:6])=[O;H0;D1;+0:1] | null | [] | null | null | 1 | HOUR | N-{3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5-{2-[2-(methylthio)ethoxy]ethyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine (70.0 mg) was dissolved in dichloromethane (5.0 mL), titanium tetraisopropoxide (0.10 mL), methanol (0.50 mL) and 70% aqueous tert-butyl hydroperoxide solution (8.0 mL) were added, and the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Monosulfide | Sulfone | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].ClCCl | null | 1 | CC(C)(C)OO.CSCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].ClCCl>CS(=O)(=O)CCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-573e279e07c2436eae0e8b3b4f9a443a | CS(=O)(=O)CCOC(=O)ON1C(=O)CCC1=O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CS(=O)(=O)CCOC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | C(O)([O-])=O.[Na+].Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl.C(C)N(CC)CC.CS(=O)(=O)CCOC(=O)ON1C(CCC1=O)=O>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OCCS(=O)(=O)C)=O | O=C1CCC(=O)N1O[C:8]([O:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])=[O:9].[NH2:10][CH2:11][CH2:12][n:13]1[cH:14][cH:15][c:16]2[n:17][cH:18][n:19][c:20]([NH:21][c:22]3[cH:23][cH:24][c:25]([O:26][c:27]4[cH:28][cH:29][cH:30][c:31]([C:32]([F:33])([F:34])[F:35])[cH:36]4)[c:37]([Cl:38])[cH:39]3)[c:40]12>>[CH3:1][S:2](=[O:3]... | CS(=O)(=O)CCOC(=O)ON1C(=O)CCC1=O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CS(=O)(=O)CCOC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | ClCCl | Protection | OtherReaction | 90f1cd2cfb4916c247fdb0b8c4bcd653fe37fb375d251f3afd49969111cee737 | f7ec1d72774a3155b06d1cf24e018b58f69117ddf4d9559df84efc3ecef0f4d7 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O=C1-C-C-C(=O)-N-1-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 82.9 | [{"value": 82.9, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OCCS(=O)(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 5-(2-Aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (64.1 mg) and triethylamine (1.0 mL) were dissolved in dichloromethane (5.0 mL), 1-({[2-(methylsulfonyl)ethoxy]carbonyl}oxy)pyrrolidine-2,5-dione (45.6 mg) was added, and the mixture was stirred at room... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Tertiary amide.Primary amine | Carbamic ester | C1CCNC1 | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | ClCCl | null | 2 | CS(=O)(=O)CCOC(=O)ON1C(=O)CCC1=O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>ClCCl>CS(=O)(=O)CCOC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de58d98cb9084bcdb8e9ed115a06fa39 | CS(=O)(=O)CCN.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.O=C(n1ccnc1)n1ccnc1>>CS(=O)(=O)CCNC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | C(O)([O-])=O.[Na+].CS(=O)(=O)CCN.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(=O)NCCS(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][NH2:7].[NH2:10][CH2:11][CH2:12][n:13]1[cH:14][cH:15][c:16]2[n:17][cH:18][n:19][c:20]([NH:21][c:22]3[cH:23][cH:24][c:25]([O:26][c:27]4[cH:28][cH:29][cH:30][c:31]([C:32]([F:33])([F:34])[F:35])[cH:36]4)[c:37]([Cl:38])[cH:39]3)[c:40]12.c1cn([C:8](n2ccnc2)=[O:9])cn1>>[CH3:1][S:2](=... | CS(=O)(=O)CCN.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.O=C(n1ccnc1)n1ccnc1 | CS(=O)(=O)CCNC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | ClCCl.C(C)N(CC)CC | Acylation | OtherReaction | 4bbb31b0118d7292be8236579c179606942bc7ed40684e26f7727a569ab5c30d | 4ff96020857e85930fbee987c7fa4ef615e45b2ea39cff27ceaec8f9174d5b6f | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:3]-[C:2]-[C:1] | null | [] | null | null | 1 | HOUR | 5-(2-Aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (54.1 mg) and triethylamine (0.7 mL) were dissolved in dichloromethane (10 mL), 1,1′-carbonylbis(1H-imidazole) was added, and the mixture was stirred at room temperature. After 1 hr, 2-(methylsulfonyl)e... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | Other | ClCCl.C(C)N(CC)CC | null | 1 | CS(=O)(=O)CCN.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.O=C(n1ccnc1)n1ccnc1>ClCCl.C(C)N(CC)CC>CS(=O)(=O)CCNC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2507183d9084d9e93389f75e358c959 | CCN(CC)CC.CS(=O)(=O)Cl.OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CC(C)(C)SCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | C(O)([O-])=O.[Na+].C(C)N(CC)CC.CS(=O)(=O)Cl.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCCO.O1CCCC1>>C(C)(C)(C)SCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl | CCN(C[CH3:1])C[CH3:4].O=[S:5](=O)(Cl)[CH3:2].O[CH2:6][CH2:7][O:8][CH2:9][CH2:10][n:11]1[cH:12][cH:13][c:14]2[n:15][cH:16][n:17][c:18]([NH:19][c:20]3[cH:21][cH:22][c:23]([O:24][c:25]4[cH:26][cH:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34]4)[c:35]([Cl:36])[cH:37]3)[c:38]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[S:5][CH... | CCN(CC)CC.CS(=O)(=O)Cl.OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CC(C)(C)SCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 35166abb9de0619a8f187a74768c2f6aceafeb24e7b93e0d8fdb401099bb2899 | e3d4d52c36c59c07e4cb776c40a7ed3714122b74ff154496ff99e60200705191 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C-N(-C-[CH3;D1;+0:1])-C-[CH3;D1;+0:2].Cl-[S;H0;D4;+0:3](=O)(=O)-[CH3;D1;+0:4].O-[CH2;D2;+0:5]-[C:6]-[#8:7]>>[#8:7]-[C:6]-[CH2;D2;+0:5]-[S;H0;D2;+0:3]-[C;H0;D4;+0:4](-[C;D1;H3:8])(-[CH3;D1;+0:1])-[CH3;D1;+0:2] | null | [] | null | null | 1 | HOUR | 2-{2-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethoxy}ethanol (150 mg) was dissolved in tetrahydrofuran (6.0 mL), and triethylamine (1.00 mL) and methanesulfonyl chloride (0.59 mL) were added under ice-cooling and the mixture was stirred for 1 hr. Saturated aqueous sodium... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary amine.Sulfonyl halide | Monosulfide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | null | null | 1 | CCN(CC)CC.CS(=O)(=O)Cl.OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CC(C)(C)SCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-daed46c44a574664a133a43f299261c4 | CC(C)(C)OO.CC(C)(C)SCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CC(C)(C)S(=O)(=O)CCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | S(=S)(=O)([O-])[O-].[Na+].[Na+].CO.C(C)(C)(C)OO.C(C)(C)(C)SCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl>>C(C)(C)(C)S(=O)(=O)CCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl | CC(C)(C)O[OH:7].[CH3:1][C:2]([CH3:3])([CH3:4])[S:5][CH2:8][CH2:9][O:10][CH2:11][CH2:12][n:13]1[cH:14][cH:15][c:16]2[n:17][cH:18][n:19][c:20]([NH:21][c:22]3[cH:23][cH:24][c:25]([O:26][c:27]4[cH:28][cH:29][cH:30][c:31]([C:32]([F:33])([F:34])[F:35])[cH:36]4)[c:37]([Cl:38])[cH:39]3)[c:40]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[... | CC(C)(C)OO.CC(C)(C)SCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CC(C)(C)S(=O)(=O)CCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4] | ClCCl | Oxidation | OtherReaction | 73ca5438c687e7554e6372a79a1d180e809287a4397486487708df09a5fd20e0 | ebe5803abbd530cb5af8bdb9d457c04c55bf786787bd2848bd344ab633fecdcb | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-O-[OH;D1;+0:1].[C:2]-[C:3]-[S;H0;D2;+0:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8]>>[C:2]-[C:3]-[S;H0;D4;+0:4](=[O;D1;H0:9])(=[O;H0;D1;+0:1])-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8] | null | [] | null | null | 1 | HOUR | 5-{2-[2-(tert-Butylthio)ethoxy]ethyl}-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine (140 mg) was dissolved in dichloromethane (5.0 mL), titanium tetraisopropoxide (0.90 mL), methanol (0.20 mL) and 70% aqueous tert-butyl hydroperoxide solution (7.0 mL) were added, and the mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Monosulfide | Sulfone | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].ClCCl | null | 1 | CC(C)(C)OO.CC(C)(C)SCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].ClCCl>CC(C)(C)S(=O)(=O)CCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-80d75f639085448fa4e4b23a2c3e8e72 | OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.OCC[S-]>>O=S(CCO)CCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | ClC1=CC(=CC=C1)C(=O)OO.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCCO.OCC[S-].[Na+].C(O)([O-])=O.[Na+]>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCCS(=O)CCO | O[CH2:6][CH2:7][O:8][CH2:9][CH2:10][n:11]1[cH:12][cH:13][c:14]2[n:15][cH:16][n:17][c:18]([NH:19][c:20]3[cH:21][cH:22][c:23]([O:24][c:25]4[cH:26][cH:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34]4)[c:35]([Cl:36])[cH:37]3)[c:38]12.[S-:2][CH2:3][CH2:4][OH:5]>>[O:1]=[S:2]([CH2:3][CH2:4][OH:5])[CH2:6][CH2:7][O:8][CH2... | OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.OCC[S-] | O=S(CCO)CCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | ClCCl.O1CCCC1.CN(C=O)C | Oxidation | OtherReaction | cf490f2816244d18f6b40e187d410c6f448592ffc671c83df1c0f56de3c17a78 | a113504bc7984867183625e9ff75fa106d4aacaf0008eec901f3292d417d672c | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[S-;H0;D1:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D3;+0:6](=[O;D1;H0:7])-[C:5]-[C:4] | null | [] | null | null | 5 | HOUR | The compound (120 mg) obtained by the reaction in the same manner as in Example 172 (i) using the compound (200 mg) of Example 147, sodium 2-hydroxyethanethiolate (2.02 g), tetrahydrofuran (6.0 mL) and N,N-dimethylformamide (5.0 mL) was dissolved in dichloromethane (7.0 mL). m-Chloroperbenzoic acid (110 mg) was added a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Sulfoxide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | null | ClCCl.O1CCCC1.CN(C=O)C | null | 5 | OCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.OCC[S-]>ClCCl.O1CCCC1.CN(C=O)C>O=S(CCO)CCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-742df502db25418c93d4e206d08e4994 | CS(=O)(=O)CS(=O)(=O)Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CS(=O)(=O)CS(=O)(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | C(O)([O-])=O.[Na+].Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl.CN1CCOCC1.CS(=O)(=O)CS(=O)(=O)Cl>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNS(=O)(=O)CS(=O)(=O)C | Cl[S:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])(=[O:7])=[O:8].[NH2:9][CH2:10][CH2:11][n:12]1[cH:13][cH:14][c:15]2[n:16][cH:17][n:18][c:19]([NH:20][c:21]3[cH:22][cH:23][c:24]([O:25][c:26]4[cH:27][cH:28][cH:29][c:30]([C:31]([F:32])([F:33])[F:34])[cH:35]4)[c:36]([Cl:37])[cH:38]3)[c:39]12>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][... | CS(=O)(=O)CS(=O)(=O)Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CS(=O)(=O)CS(=O)(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[#16:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[#16:5]-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:8]-[C:7]-[C:6] | null | [] | null | null | 1 | HOUR | 5-(2-Aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (245 mg) and N-methylmorpholine (1.0 mL) were dissolved in dichloromethane (6.0 mL), (methylsulfonyl)methanesulfonyl chloride (0.40 mL) was added dropwise under ice-cooling, and the mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 1 | CS(=O)(=O)CS(=O)(=O)Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>ClCCl>CS(=O)(=O)CS(=O)(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f54fe403840b4db7bc828ad07e9330b7 | N#Cc1cccc(Oc2ccc(N)cc2Cl)c1.c1ccc(Oc2ncnc3cc4n(c23)CCOC4)cc1>>N#Cc1cccc(Oc2ccc(Nc3ncnc4cc5n(c34)CCOC5)cc2Cl)c1 | O(C1=CC=CC=C1)C1=NC=NC=2C=C3COCCN3C21.NC1=CC(=C(OC=2C=C(C#N)C=CC2)C=C1)Cl.Cl.N1=CC=CC=C1.CN1C(CCC1)=O>>Cl.ClC1=C(OC=2C=C(C#N)C=CC2)C=CC(=C1)NC1=NC=NC=2C=C3COCCN3C21 | [N:2]#[C:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][c:13]([NH2:14])[cH:28][c:29]2[Cl:30])[cH:31]1.c1ccc(O[c:15]2[n:16][cH:17][n:18][c:19]3[cH:20][c:21]4[n:22]([c:23]23)[CH2:24][CH2:25][O:26][CH2:27]4)cc1>>[N:2]#[C:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][c:13]([NH:14][c:15]3[n:16][cH:1... | N#Cc1cccc(Oc2ccc(N)cc2Cl)c1.c1ccc(Oc2ncnc3cc4n(c23)CCOC4)cc1 | N#Cc1cccc(Oc2ccc(Nc3ncnc4cc5n(c34)CCOC5)cc2Cl)c1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Displacement of ethoxy group by primary amine | 4e8c49b6a53a25f3e422d174bad770cad826ab655dbca988f7404aa7fb4749ff | 953ca34981f329c845365ec5b25a3d27fa72aebd3e467f4e6ef8becba38a9d76 | c1ccc(Oc2ccc(Nc3ncnc4cc5n(c34)CCOC5)cc2)cc1 | [C:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-O-c3:c:c:c:c:c:3):[c:10]:1:2.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 91.8 | [{"value": 91.8, "product": "Cl.ClC1=C(OC=2C=C(C#N)C=CC2)C=CC(=C1)NC1=NC=NC=2C=C3COCCN3C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 14 | HOUR | A mixture of 4-phenoxy-6,7-dihydro-9H-pyrimido[4′,5′:4,5]pyrrolo[2,1-c][1,4]oxazine (69 mg), 3-(4-amino-2-chlorophenoxy)benzonitrile (95 mg), pyridine hydrochloride (75 mg) and 1-methyl-2-pyrrolidone (1 mL) was stirred at 140° C. for 14 hrs. After the completion of the reaction, the mixture was diluted with ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary amine | c1ccccc1.c1ncc2c(cc3n2CCOC3)n1 | c1ncc2c(cc3n2CCOC3)n1 | c1ccccc1.c1ccccc1.c1ncc2c(cc3n2CCOC3)n1 | HO- | C(C)(=O)OCC | 140 | 14 | N#Cc1cccc(Oc2ccc(N)cc2Cl)c1.c1ccc(Oc2ncnc3cc4n(c23)CCOC4)cc1>C(C)(=O)OCC>N#Cc1cccc(Oc2ccc(Nc3ncnc4cc5n(c34)CCOC5)cc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9683767a1de411198699e4e567fcad7 | CCOC(CBr)OCC.Clc1ncnc2cc[nH]c12>>CCOC(Cn1ccc2ncnc(Cl)c21)OCC | ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+].BrCC(OCC)OCC>>ClC=1C2=C(N=CN1)C=CN2CC(OCC)OCC | Br[CH2:5][CH:4]([O:3][CH2:2][CH3:1])[O:16][CH2:17][CH3:18].[nH:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([Cl:14])[c:15]12>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([Cl:14])[c:15]12)[O:16][CH2:17][CH3:18] | CCOC(CBr)OCC.Clc1ncnc2cc[nH]c12 | CCOC(Cn1ccc2ncnc(Cl)c21)OCC | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | Br-[CH2;D2;+0:1]-[C:2](-[#8:3])-[#8:4].[Cl;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]2:[c:11]:[c:12]:[nH;D2;+0:13]:[c:14]:1:2>>[#8:3]-[C:2](-[#8:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]2:[#7;a:9]:[c:8]:[#7;a:7]:[c:6](-[Cl;D1;H0:5]):[c:14]:2:1 | null | [] | 80 | CELSIUS | 4.5 | HOUR | 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (1 g) was dissolved in N,N-dimethylformamide (13 mL), cesium carbonate (6.37 g) and 2-bromo-1,1-diethoxyethane (2.94 mL) were sequentially added and the mixture was stirred at 80° C. for 4.5 hrs. The reaction mixture was diluted with ethyl acetate (100 mL), and washed with water (80... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HBr | CN(C=O)C.C(C)(=O)OCC | 80 | 4.5 | CCOC(CBr)OCC.Clc1ncnc2cc[nH]c12>CN(C=O)C.C(C)(=O)OCC>CCOC(Cn1ccc2ncnc(Cl)c21)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-821be8c2d6984369a964ef3cbc9d90ad | CCOC(Cn1ccc2ncnc(Cl)c21)OCC.Oc1ccccc1>>CCOC(Cn1ccc2ncnc(Oc3ccccc3)c21)OCC | ClC=1C2=C(N=CN1)C=CN2CC(OCC)OCC.C1(=CC=CC=C1)O.C([O-])([O-])=O.[K+].[K+].CN1C(CCC1)=O>>O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=CN2CC(OCC)OCC | Cl[c:13]1[n:12][cH:11][n:10][c:9]2[cH:8][cH:7][n:6]([CH2:5][CH:4]([O:3][CH2:2][CH3:1])[O:22][CH2:23][CH3:24])[c:21]21.[OH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([O:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]12)[O:22][C... | CCOC(Cn1ccc2ncnc(Cl)c21)OCC.Oc1ccccc1 | CCOC(Cn1ccc2ncnc(Oc3ccccc3)c21)OCC | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e413f3f37b0860f9114d381e2229b3cb26eec6cbb13fb270088c627125645da2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ncnc3cc[nH]c23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 94.7 | [{"value": 94.7, "product": "O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=CN2CC(OCC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | A mixture of 4-chloro-5-(2,2-diethoxyethyl)-5H-pyrrolo[3,2-d]pyrimidine (1 g), phenol (420 mg), potassium carbonate (617 mg) and 1-methyl-2-pyrrolidone (6.74 mL) was stirred with heating at 140° C. for 6 hrs. The reaction mixture was diluted with ethyl acetate (100 mL), and washed with water (80 mL). The organic layer ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1 | HCl | C(C)(=O)OCC | 140 | null | CCOC(Cn1ccc2ncnc(Cl)c21)OCC.Oc1ccccc1>C(C)(=O)OCC>CCOC(Cn1ccc2ncnc(Oc3ccccc3)c21)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ed20c16b76af4d9ebf8c78660bbf7299 | CCOC(Cn1ccc2ncnc(Oc3ccccc3)c21)OCC>>OC(O)Cn1ccc2ncnc(Oc3ccccc3)c21 | O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=CN2CC(OCC)OCC>>O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=CN2CC(O)O | CC[O:1][CH:2]([O:3]CC)[CH2:4][n:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11][c:12]([O:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:20]12>>[OH:1][CH:2]([OH:3])[CH2:4][n:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11][c:12]([O:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:20]12 | CCOC(Cn1ccc2ncnc(Oc3ccccc3)c21)OCC | OC(O)Cn1ccc2ncnc(Oc3ccccc3)c21 | null | null | ClCCl.FC(C(=O)O)(F)F | Deprotection | OtherReaction | eeceb6d8d193a50399e6a659d362244161c0eb3f47aa91714500cb7a2b797e77 | 3cb0396ca8ad36859ee8d51a67a558871ec1b96bb69d5cbac40dafd7041336b3 | c1ccc(Oc2ncnc3cc[nH]c23)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])-[O;H0;D2;+0:4]-C-C>>[C:3]-[C:2](-[OH;D1;+0:1])-[OH;D1;+0:4] | 90.6 | [{"value": 90.6, "product": "O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=CN2CC(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 4-Phenoxy-5-(2,2-diethoxyethyl)-5H-pyrrolo[3,2-d]pyrimidine (1.1 g) was dissolved in dichloromethane (4.53 mL)/trifluoroacetic acid (4.53 mL), and the mixture was stirred at room temperature for 16 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (100 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Secondary alcohol.Secondary alcohol | null | null | c1ncnc2cc[nH]c12.c1ccccc1 | Other | ClCCl.FC(C(=O)O)(F)F | null | 16 | CCOC(Cn1ccc2ncnc(Oc3ccccc3)c21)OCC>ClCCl.FC(C(=O)O)(F)F>OC(O)Cn1ccc2ncnc(Oc3ccccc3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97a9c812880c4aabab994785fa96147a | CS(=O)(=O)CCN.OC(O)Cn1ccc2ncnc(Oc3ccccc3)c21>>CS(=O)(=O)CCNCCn1ccc2ncnc(Oc3ccccc3)c21 | O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=CN2CC(O)O.CS(=O)(=O)CCN.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>CS(=O)(=O)CCNCCN1C=CC=2N=CN=C(C21)OC2=CC=CC=C2 | [CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][NH2:7].O[CH:8](O)[CH2:9][n:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][n:16][c:17]([O:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]12>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][NH:7][CH2:8][CH2:9][n:10]1[cH:11][cH:12][c:13]2[n:14][cH:15][n:16][c:17]([O:18][c:19]3[cH:20][cH... | CS(=O)(=O)CCN.OC(O)Cn1ccc2ncnc(Oc3ccccc3)c21 | CS(=O)(=O)CCNCCn1ccc2ncnc(Oc3ccccc3)c21 | null | null | C(C)(=O)O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 1005605d97265006976847b789e229ac5cd3703fcca95c744cbf92dc830ad4e1 | 71c2fa0a05d43a3890a8fa4b0b567605c4a5f5eac1b9e0f4b85fa1e29c40215a | c1ccc(Oc2ncnc3cc[nH]c23)cc1 | O-[CH;D3;+0:1](-O)-[C:2]-[#7;a:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[#7;a:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | 76.5 | [{"value": 76.5, "product": "CS(=O)(=O)CCNCCN1C=CC=2N=CN=C(C21)OC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 2-(4-Phenoxy-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethane-1,1-diol (500 mg) and 2-(methylsulfonyl)ethylamine (341 mg) were dissolved in N,N-dimethylformamide (29 mL)/acetic acid (2.9 mL), and the mixture was stirred at room temperature for 1.5 hrs. Sodium triacetoxyborohydride (579 mg) was added, and the mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol.Primary amine | Secondary amine | null | null | c1ncnc2cc[nH]c12.c1ccccc1 | HO- | C(C)(=O)O.CN(C=O)C | null | 1.5 | CS(=O)(=O)CCN.OC(O)Cn1ccc2ncnc(Oc3ccccc3)c21>C(C)(=O)O.CN(C=O)C>CS(=O)(=O)CCNCCn1ccc2ncnc(Oc3ccccc3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c35dce8966694167a5409f83e333cbdb | Cc1ccc(Oc2ccc(N)cc2C(F)(F)F)cn1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1>>Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2C(F)(F)F)cn1 | C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)Cl.CC1=CC=C(C=N1)OC1=C(C=C(N)C=C1)C(F)(F)F.CN1C(CCC1)=O>>CC1=CC=C(C=N1)OC1=C(C=C(C=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO)C(F)(F)F | [CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:27][c:28]2[C:29]([F:30])([F:31])[F:32])[cH:33][n:34]1.O=C(c1ccccc1)[O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][n:19]1[cH:18][cH:17][c:16]2[n:15][cH:14][n:13][c:12](Cl)[c:26]21>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([NH:11]... | Cc1ccc(Oc2ccc(N)cc2C(F)(F)F)cn1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1 | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2C(F)(F)F)cn1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | e83d3b14c87cd29b2801fdf995368b0a2da0018f312296eb02835cf026e36ef5 | 03164802232677317a7efd0e24d53056dbf9714f8e35a1ee2da95661003b43d6 | c1cncc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.O=C(-[O;H0;D2;+0:11]-[C:12]-[C:13])-c1:c:c:c:c:c:1.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17]):[c:10]:1:2.[C:13]-[C:12]-[O... | 57.5 | [{"value": 57.5, "product": "CC1=CC=C(C=N1)OC1=C(C=C(C=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | A mixture of 2-[2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy]ethyl benzoate (150 mg), 4-[(6-methylpyridin-3-yl)oxy]-3-(trifluoromethyl)aniline (175 mg) and 1-methyl-2-pyrrolidone (0.863 mL) was stirred with heating at 140° C. for 2.5 hrs. The reaction mixture was diluted with ethyl acetate (80 mL) and washed with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Primary alcohol.Secondary amine | c1ccccc1.c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ccncc1.c1ccccc1.c1ncnc2cc[nH]c12 | HCl | C(C)(=O)OCC | 140 | null | Cc1ccc(Oc2ccc(N)cc2C(F)(F)F)cn1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1>C(C)(=O)OCC>Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2C(F)(F)F)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b87f91bae654f2089a442ee8b694ba5 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Cc1cc(N)ccc1Oc1cccc(C(F)(F)F)c1>>Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(C(F)(F)F)c1 | C(C)(C)(C)OC(NCCN1C=CC=2N=CN=C(C21)Cl)=O.CC=1C=C(N)C=CC1OC1=CC(=CC=C1)C(F)(F)F.C(C)(C)O>>CC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O | Cl[c:6]1[n:7][cH:8][n:9][c:10]2[cH:11][cH:12][n:13]([CH2:14][CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]12.[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:25][cH:26][c:27]1[O:28][c:29]1[cH:30][cH:31][cH:32][c:33]([C:34]([F:35])([F:36])[F:37])[cH:38]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:... | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Cc1cc(N)ccc1Oc1cccc(C(F)(F)F)c1 | Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(C(F)(F)F)c1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 100 | [{"value": 100.0, "product": "CC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | A mixture of tert-butyl[2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethyl]carbamate (297 mg), 3-methyl-4-[3-(trifluoromethyl)phenoxy]aniline (401 mg) and isopropyl alcohol (2.97 mL) was stirred at 80° C. for 16 hrs. The reaction mixture was diluted with ethyl acetate (80 mL), and washed with aqueous sodium hydrogen car... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1 | HCl | C(C)(=O)OCC | 80 | 16 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Cc1cc(N)ccc1Oc1cccc(C(F)(F)F)c1>C(C)(=O)OCC>Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b5b4e588478c40978f5d7d634f8e6c6f | Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(C(F)(F)F)c1>>Cc1cc(Nc2ncnc3ccn(CCN)c23)ccc1Oc1cccc(C(F)(F)F)c1 | CC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O.FC(C(=O)O)(F)F>>NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)C | CC(C)(C)OC(=O)[NH:16][CH2:15][CH2:14][n:13]1[cH:12][cH:11][c:10]2[n:9][cH:8][n:7][c:6]([NH:5][c:4]3[cH:3][c:2]([CH3:1])[c:20]([O:21][c:22]4[cH:23][cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31]4)[cH:19][cH:18]3)[c:17]21>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][n:9][c:10]3[cH:11][cH:12][n:13]([CH2:14]... | Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(C(F)(F)F)c1 | Cc1cc(Nc2ncnc3ccn(CCN)c23)ccc1Oc1cccc(C(F)(F)F)c1 | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 110.4 | [{"value": 110.4, "product": "NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | tert-Butyl {2-[4-({3-methyl-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}carbamate (494 mg) was dissolved in dichloromethane (6.4 mL), trifluoroacetic acid (4.8 mL) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduc... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1 | HO- | ClCCl | null | 1 | Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(C(F)(F)F)c1>ClCCl>Cc1cc(Nc2ncnc3ccn(CCN)c23)ccc1Oc1cccc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7042f678f4e24b7e8475ebfd78157a53 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Cc1cc(N)ccc1Oc1cccc(OC(F)(F)F)c1>>Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(OC(F)(F)F)c1 | C(C)(C)(C)OC(NCCN1C=CC=2N=CN=C(C21)Cl)=O.CC=1C=C(N)C=CC1OC1=CC(=CC=C1)OC(F)(F)F>>CC=1C=C(C=CC1OC1=CC(=CC=C1)OC(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O | Cl[c:6]1[n:7][cH:8][n:9][c:10]2[cH:11][cH:12][n:13]([CH2:14][CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]12.[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:25][cH:26][c:27]1[O:28][c:29]1[cH:30][cH:31][cH:32][c:33]([O:34][C:35]([F:36])([F:37])[F:38])[cH:39]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:... | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Cc1cc(N)ccc1Oc1cccc(OC(F)(F)F)c1 | Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(OC(F)(F)F)c1 | null | null | C(C)(C)O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 103.5 | [{"value": 103.5, "product": "CC=1C=C(C=CC1OC1=CC(=CC=C1)OC(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | tert-Butyl[2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethyl]carbamate (297 mg) and 3-methyl-4-[3-(trifluoromethoxy)phenoxy]aniline (425 mg) were dissolved in isopropyl alcohol (2.97 mL), and the mixture was stirred at 80° C. for 16 hrs. After cooling to room temperature, the mixture was diluted with ethyl acetate (60 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1 | HCl | C(C)(C)O.C(C)(=O)OCC | 80 | 16 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Cc1cc(N)ccc1Oc1cccc(OC(F)(F)F)c1>C(C)(C)O.C(C)(=O)OCC>Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(OC(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a6e290e4fd34767918c1d46929b1e67 | Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(OC(F)(F)F)c1>>Cc1cc(Nc2ncnc3ccn(CCN)c23)ccc1Oc1cccc(OC(F)(F)F)c1 | CC=1C=C(C=CC1OC1=CC(=CC=C1)OC(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O.FC(C(=O)O)(F)F>>NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)OC(F)(F)F)C | CC(C)(C)OC(=O)[NH:16][CH2:15][CH2:14][n:13]1[cH:12][cH:11][c:10]2[n:9][cH:8][n:7][c:6]([NH:5][c:4]3[cH:3][c:2]([CH3:1])[c:20]([O:21][c:22]4[cH:23][cH:24][cH:25][c:26]([O:27][C:28]([F:29])([F:30])[F:31])[cH:32]4)[cH:19][cH:18]3)[c:17]21>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][n:9][c:10]3[cH:11][cH:12][n:13]([C... | Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(OC(F)(F)F)c1 | Cc1cc(Nc2ncnc3ccn(CCN)c23)ccc1Oc1cccc(OC(F)(F)F)c1 | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 98.4 | [{"value": 98.4, "product": "NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)OC(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | tert-Butyl {2-[4-({3-methyl-4-[3-(trifluoromethoxy)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}carbamate (523 mg) was dissolved in dichloromethane (6.4 mL), trifluoroacetic acid (4.8 mL) was added, and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated under red... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1 | HO- | ClCCl | null | 2 | Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(OC(F)(F)F)c1>ClCCl>Cc1cc(Nc2ncnc3ccn(CCN)c23)ccc1Oc1cccc(OC(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64dfd18dc4ec4c9bbf887d4e844efbe0 | CS(=O)(=O)CC(=O)O.Cc1cc(Nc2ncnc3ccn(CCN)c23)ccc1Oc1cccc(OC(F)(F)F)c1>>Cc1cc(Nc2ncnc3ccn(CCNC(=O)CS(C)(=O)=O)c23)ccc1Oc1cccc(OC(F)(F)F)c1 | NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)OC(F)(F)F)C.CS(=O)(=O)CC(=O)O.Cl.C(C)N=C=NCCCN(C)C.O.ON1N=NC2=C1C=CC=C2>>CS(=O)(=O)CC(=O)NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)OC(F)(F)F)C | O[C:17](=[O:18])[CH2:19][S:20]([CH3:21])(=[O:22])=[O:23].[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][n:9][c:10]3[cH:11][cH:12][n:13]([CH2:14][CH2:15][NH2:16])[c:24]23)[cH:25][cH:26][c:27]1[O:28][c:29]1[cH:30][cH:31][cH:32][c:33]([O:34][C:35]([F:36])([F:37])[F:38])[cH:39]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7... | CS(=O)(=O)CC(=O)O.Cc1cc(Nc2ncnc3ccn(CCN)c23)ccc1Oc1cccc(OC(F)(F)F)c1 | Cc1cc(Nc2ncnc3ccn(CCNC(=O)CS(C)(=O)=O)c23)ccc1Oc1cccc(OC(F)(F)F)c1 | null | null | C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#16:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#16:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 41.8 | [{"value": 41.8, "product": "CS(=O)(=O)CC(=O)NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)OC(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-(2-aminoethyl)-N-{3-methyl-4-[3-(trifluoromethoxy)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine (174 mg), 2-(methylsulfonyl)acetic acid (54 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (112 mg), 1-hydroxybenzotriazole monohydrate (79 mg) and triethylamine (0.273 mL) in N,N-dimet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1 | HO- | C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | null | null | CS(=O)(=O)CC(=O)O.Cc1cc(Nc2ncnc3ccn(CCN)c23)ccc1Oc1cccc(OC(F)(F)F)c1>C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC>Cc1cc(Nc2ncnc3ccn(CCNC(=O)CS(C)(=O)=O)c23)ccc1Oc1cccc(OC(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a014a61d94243c2b4e9ac2afb3ee61a | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(Cl)c2)c(Cl)c1>>CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 | ClC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)Cl.C(O)([O-])=O.[Na+]>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)Cl)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O | Cl[c:18]1[n:17][cH:16][n:15][c:14]2[cH:13][cH:12][n:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:35]21.[NH2:19][c:20]1[cH:21][cH:22][c:23]([O:24][c:25]2[cH:26][cH:27][cH:28][c:29]([Cl:30])[cH:31]2)[c:32]([Cl:33])[cH:34]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:... | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(Cl)c2)c(Cl)c1 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 81.9 | [{"value": 81.9, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)Cl)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 15 | HOUR | A mixture of tert-butyl 2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethylcarbamate (1.19 g), 3-chloro-4-(3-chlorophenoxy)aniline (1.22 g) and isopropyl alcohol (12.0 mL) was stirred at 80° C. for 15 hrs. Under ice-cooling, aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. Th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(C)(C)O | 80 | 15 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(Cl)c2)c(Cl)c1>C(C)(C)O>CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3e2771a034c4be097d86b1f385032a8 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21>>Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 | ClC=1C=C(C=CC1OC1=CC(=CC=C1)Cl)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O.Cl>>Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)Cl)Cl | CC(C)(C)OC(=O)[NH:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]([O:19][c:20]4[cH:21][cH:22][cH:23][c:24]([Cl:2])[cH:26]4)[c:27]([Cl:28])[cH:29]3)[c:30]12>>[ClH:2].[NH2:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][cH:17][c:... | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 | Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 | null | null | O1CCCC1 | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | f9b0ddd5e086b40f0768881f9b226acdc5a9dc29f99a9283af567e925b55a3d7 | b15a28c2a3fd58b98c3a6c1b435f8c25519aeb02339cc9ac8ff8fecd35099d5c | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].[Cl;H0;D1;+0:4]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]>>[C:3]-[C:2]-[NH2;D1;+0:1].[Cl;D1;H0:10]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[ClH;D0;+0:4] | null | [] | 65 | CELSIUS | 18 | HOUR | To a solution of tert-butyl 2-(4-{[3-chloro-4-(3-chlorophenoxy)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethylcarbamate (1.69 g) in tetrahydrofuran (32 mL) was added 2N hydrochloric acid (16 mL). The reaction mixture was stirred at 65° C. for 18 hrs and concentrated. Ethanol was added, and the mixture was concentra... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boc | Aromatic halide.Primary amine | c1ccccc1 | c1ccccc1 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | 65 | 18 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21>O1CCCC1>Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b38e8a4f5994c488a45f0d2128f3e91 | CS(=O)(=O)CC(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21>>CS(=O)(=O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 | Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)Cl)Cl.CS(=O)(=O)CC(=O)O.ON1N=NC2=C1C=CC=C2.Cl.C(C)N=C=NCCCN(C)C>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)Cl)NC=1C2=C(N=CN1)C=CN2CCNC(CS(=O)(=O)C)=O | O[C:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])=[O:7].[NH2:8][CH2:9][CH2:10][n:11]1[cH:12][cH:13][c:14]2[n:15][cH:16][n:17][c:18]([NH:19][c:20]3[cH:21][cH:22][c:23]([O:24][c:25]4[cH:26][cH:27][cH:28][c:29]([Cl:30])[cH:31]4)[c:32]([Cl:33])[cH:34]3)[c:35]12>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][C:6](=[O:7])[NH:8][CH2:9][CH2:1... | CS(=O)(=O)CC(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 | CS(=O)(=O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 | null | null | O.C(C)N(CC)CC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#16:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#16:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 68.8 | [{"value": 68.8, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)Cl)NC=1C2=C(N=CN1)C=CN2CCNC(CS(=O)(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 5-(2-aminoethyl)-N-[3-chloro-4-(3-chlorophenoxy)phenyl]-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (200 mg), 2-(methylsulfonyl)acetic acid (113 mg) and 1-hydroxybenzotriazole (122 mg) in N,N-dimethylformamide (5.0 mL) were added a solution of triethylamine (419 mg) in N,N-dimethylformamide (1.2... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O.C(C)N(CC)CC.CN(C=O)C | null | 16 | CS(=O)(=O)CC(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21>O.C(C)N(CC)CC.CN(C=O)C>CS(=O)(=O)CC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(Cl)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-20b9bc27794b4a318c30b0fc7a348295 | ClCCCBr.Clc1ncnc2cc[nH]c12>>ClCCCn1ccc2ncnc(Cl)c21 | O.BrCCCCl.ClC=1C2=C(N=CN1)C=CN2.C([O-])([O-])=O.[Cs+].[Cs+]>>ClC=1C2=C(N=CN1)C=CN2CCCCl | Br[CH2:4][CH2:3][CH2:2][Cl:1].[nH:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11][c:12]([Cl:13])[c:14]12>>[Cl:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11][c:12]([Cl:13])[c:14]12 | ClCCCBr.Clc1ncnc2cc[nH]c12 | ClCCCn1ccc2ncnc(Cl)c21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5](-[Cl;D1;H0:4]):[c:13]:2:1 | 81 | [{"value": 81.0, "product": "ClC=1C2=C(N=CN1)C=CN2CCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (1.54 g) in N,N-dimethylformamide (20 mL) was added cesium carbonate (4.89 g) under ice-cooling, and the mixture was stirred under ice-cooling for 20 min. 1-Bromo-3-chloropropane (1.89 g) was added and the mixture was stirred under ice-cooling for 1 hr and at room t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HBr | CN(C=O)C | null | null | ClCCCBr.Clc1ncnc2cc[nH]c12>CN(C=O)C>ClCCCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-91dc9102b7f34636ba1dcb54a14af106 | ClCCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>Fc1cccc(COc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1 | ClC=1C2=C(N=CN1)C=CN2CCCCl.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCCCl | Cl[c:14]1[n:15][cH:16][n:17][c:18]2[cH:19][cH:20][n:21]([CH2:22][CH2:23][CH2:24][Cl:25])[c:26]12.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:27][c:28]2[Cl:29])[cH:30]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH:13][c:14]3[n:15][cH:16][n:17][... | ClCCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | Fc1cccc(COc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 73.3 | [{"value": 73.3, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1.5 | HOUR | A mixture of 4-chloro-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidine (839 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (1.10 g) and isopropyl alcohol (5 mL) was stirred at 80° C. for 1.5 hrs. The mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate (30 mL) was added to the residu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ccccc1.c1ccccc1.c1ncnc2cc[nH]c12 | HCl | C(C)(C)O | 80 | 1.5 | ClCCCn1ccc2ncnc(Cl)c21.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>C(C)(C)O>Fc1cccc(COc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae8cc554d3124f4792093edaf161355d | CNCCO.Fc1cccc(COc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1>>CN(CCO)CCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21.Cl.Cl | ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCCCl.CNCCO>>Cl.Cl.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCCN(CCO)C | [CH3:1][NH:2][CH2:3][CH2:4][OH:5].[CH2:6]([CH2:7][CH2:8][n:9]1[cH:10][cH:11][c:12]2[n:13][cH:14][n:15][c:16]([NH:17][c:18]3[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]4[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]4)[c:31]([Cl:32])[cH:33]3)[c:34]12)[Cl:35]>>[CH3:1][N:2]([CH2:3][CH2:4][OH:5])[CH2:6][CH2:7][CH2:8][n:9]1[cH:10][... | CNCCO.Fc1cccc(COc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1 | CN(CCO)CCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21.Cl.Cl | null | null | CN(C=O)C | Functional Group Addition | N-alkylation of secondary amines with alkyl halides | 6dc67fdaa84d3f88aea31bd6d36481dd1f7dd6caece2acc0ef2660765ea75733 | 44df6a34ed503be8d571d8a086699e2116e82b962d53e34ea90b7759e699f35c | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:3]-[C:2]-[C:1].[ClH;D0;+0:4] | 197.9 | [{"value": 197.9, "product": "Cl.Cl.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCCN(CCO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 64 | HOUR | A mixture of N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (634 mg), 2-methylaminoethanol (534 mg) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 64 hrs. After concentration under reduced pressure, saturated aqueous sodium hydrogen carbonate (10 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | Other | CN(C=O)C | null | 64 | CNCCO.Fc1cccc(COc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1>CN(C=O)C>CN(CCO)CCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c97bb3e0f6c4c0088416cdd053dd9eb | CNC.Fc1cccc(COc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1>>CN(C)CCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21.Cl.Cl | CNC.O1CCCC1.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCCCl.CNC.O1CCCC1.C(O)([O-])=O.[Na+].CNC.O1CCCC1>>Cl.Cl.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCCN(C)C | [CH3:1][NH:2][CH3:3].[CH2:4]([CH2:5][CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]4[cH:23][cH:24][cH:25][c:26]([F:27])[cH:28]4)[c:29]([Cl:30])[cH:31]3)[c:32]12)[Cl:33]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:1... | CNC.Fc1cccc(COc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1 | CN(C)CCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21.Cl.Cl | null | null | null | Functional Group Addition | N-alkylation of secondary amines with alkyl halides | 6dc67fdaa84d3f88aea31bd6d36481dd1f7dd6caece2acc0ef2660765ea75733 | 44df6a34ed503be8d571d8a086699e2116e82b962d53e34ea90b7759e699f35c | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | [C;D1;H3:1]-[NH;D2;+0:2]-[C;D1;H3:3].[C:4]-[C:5]-[CH2;D2;+0:6]-[Cl;H0;D1;+0:7]>>[C:4]-[C:5]-[CH2;D2;+0:6]-[N;H0;D3;+0:2](-[C;D1;H3:1])-[C;D1;H3:3].[ClH;D0;+0:7] | null | [] | null | null | 26 | HOUR | N-{3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (560 mg) was dissolved in 2.0 M dimethylamine-tetrahydrofuran solution (5 mL), and the mixture was stirred at room temperature for 26 hrs. A 2.0 M dimethylamine-tetrahydrofuran solution (5 mL) was further added and the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | Other | null | null | 26 | CNC.Fc1cccc(COc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1>>CN(C)CCCn1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34250a49fb994af097be8cdb40cc5567 | CN1CCCC1=O.Fc1cccc(COc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1>>Fc1cccc(COc2ccc(N3CC4=C5C(=NC=CN5CC4)C=N3)cc2Cl)c1 | C(O)([O-])=O.[Na+].ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=CN2CCCCl.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F.CN1C(CCC1)=O>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)N1N=CC=2C=3N(CCC3C1)C=CN2 | O=C1CCCN1[CH3:14].ClC[CH2:23][CH2:22][n:21]1[c:16]2[c:15]([NH:13][c:12]3[cH:11][cH:10][c:9]([O:8][CH2:7][c:6]4[cH:5][cH:4][cH:3][c:2]([F:1])[cH:29]4)[c:27]([Cl:28])[cH:26]3)[n:25][cH:19][n:18][c:17]2[cH:24][cH:20]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][C:15]4=[C:16]5... | CN1CCCC1=O.Fc1cccc(COc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1 | Fc1cccc(COc2ccc(N3CC4=C5C(=NC=CN5CC4)C=N3)cc2Cl)c1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | c23aa5aede50162090de2ab79d35b1f935bcbe2e44e7ff413bb580b6cbb630ec | 6b5453b8fe50f89538a7d47987130d9eded8986ff745893810f6ba926047608c | C1=CN2CCC3=C2C(=N1)C=NN(c1ccc(OCc2ccccc2)cc1)C3 | Cl-C-[CH2;D2;+0:1]-[C:2]-[n;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6]2:[n;H0;D2;+0:7]:[cH;D2;+0:8]:[n;H0;D2;+0:9]:[c;H0;D3;+0:10](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c;H0;D3;+0:15]:2:1.O=C1-C-C-C-N-1-[CH3;D1;+0:16]>>[c:13]:[c:12](-[N;H0;D3;+0:11]1-[CH2;D2;+0:16]-[C;H0;D3;+0:10]2=[C;H0;D3;+0:15]3-[C;H0;D... | null | [] | 140 | CELSIUS | 1 | HOUR | A mixture of N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (839 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (1.10 g) and 1-methyl-2-pyrrolidone (5 mL) was stirred at 140° C. for 1 hr. The reaction mixture was poured into water (10 mL) and adjusted to pH 8 with saturat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amide.Secondary amine | Enamine.Enamine.Hydrazone.Substituted imine | C1CCNC1.c1ncnc2cc[nH]c12 | C1=CN2CCC3=C2C(=N1)C=N[NH]C3 | c1ccccc1.c1ccccc1.C1=CN2CCC3=C2C(=N1)C=N[NH]C3 | HCl | O | 140 | 1 | CN1CCCC1=O.Fc1cccc(COc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1>O>Fc1cccc(COc2ccc(N3CC4=C5C(=NC=CN5CC4)C=N3)cc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0beab6c844f440e7aaf3b2c5915491bc | ClCCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>>FC(F)(F)c1cccc(Oc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1 | ClC=1C2=C(N=CN1)C=CN2CCCCl.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)C(F)(F)F>>ClCCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl | Cl[c:16]1[n:17][cH:18][n:19][c:20]2[cH:21][cH:22][n:23]([CH2:24][CH2:25][CH2:26][Cl:27])[c:28]12.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([NH2:15])[cH:29][c:30]2[Cl:31])[cH:32]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([NH:15... | ClCCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1 | FC(F)(F)c1cccc(Oc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 88.5 | [{"value": 88.5, "product": "ClCCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 4.5 | HOUR | A mixture of 4-chloro-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidine (789 mg), 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (1.09 g) and isopropyl alcohol (5 mL) was stirred at 80° C. for 4.5 hrs. The mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate (30 mL) was added to the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ccccc1.c1ccccc1.c1ncnc2cc[nH]c12 | HCl | C(C)(C)O | 80 | 4.5 | ClCCCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>C(C)(C)O>FC(F)(F)c1cccc(Oc2ccc(Nc3ncnc4ccn(CCCCl)c34)cc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-50d8024f27764293a2e8f5740331e759 | CS(=O)(=O)OCCOCCOC(=O)c1ccccc1.CSc1ncnc2cn[nH]c12>>CSc1ncnc2cnn(CCOCCOC(=O)c3ccccc3)c12 | CSC=1C2=C(N=CN1)C=NN2.C(C1=CC=CC=C1)(=O)OCCOCCOS(=O)(=O)C.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>>C(C1=CC=CC=C1)(=O)OCCOCCN1N=CC=2N=CN=C(C21)SC | CS(=O)(=O)O[CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[CH3:1][S:2][c:3]1[n:4][cH:5][n:6][c:7]2[cH:8][n:9][nH:10][c:25]12>>[CH3:1][S:2][c:3]1[n:4][cH:5][n:6][c:7]2[cH:8][n:9][n:10]([CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][C:17](=[O:18])[c:19]3[cH:20][cH:21]... | CS(=O)(=O)OCCOCCOC(=O)c1ccccc1.CSc1ncnc2cn[nH]c12 | CSc1ncnc2cnn(CCOCCOC(=O)c3ccccc3)c12 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 24d3dcb41430f281b0b9d315a0380358781e9809971e0ae516154ac2e8dddf55 | 0b4f3c8c88df0a792d0db7d59004d7fe5681a61dd48ef2449ddca2d636f76ada | O=C(OCCOCCn1ncc2ncncc21)c1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#8:3].[#16:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[#7;a:11]:[nH;D2;+0:12]:[c:13]:1:2>>[#16:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[#7;a:11]:[n;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]-[#8:3]):[c:13]:1:2 | 33.1 | [{"value": 33.1, "product": "C(C1=CC=CC=C1)(=O)OCCOCCN1N=CC=2N=CN=C(C21)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | A mixture of 7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine (747 mg), 2-{2-[(methylsulfonyl)oxy]ethoxy}ethyl benzoate (1.43 g), potassium carbonate (931 mg) and N,N-dimethylformamide (12 mL) was stirred at 60° C. for 4 hrs. The reaction mixture was poured into water (30 mL), and the mixture was extracted with ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1ncc2n[nH]cc2n1 | c1ncnc2c[nH]nc12 | c1ncnc2c[nH]nc12.c1ccccc1 | MsOH.HO- | O | 60 | 4 | CS(=O)(=O)OCCOCCOC(=O)c1ccccc1.CSc1ncnc2cn[nH]c12>O>CSc1ncnc2cnn(CCOCCOC(=O)c3ccccc3)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9ad8a566a0348ecb809d8cc965cfc19 | CSc1ncnc2cnn(CCOCCOC(=O)c3ccccc3)c12.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>OCCOCCn1ncc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | C(O)([O-])=O.[Na+].C(C1=CC=CC=C1)(=O)OCCOCCN1N=CC=2N=CN=C(C21)SC.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F.Cl.N1=CC=CC=C1>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=NN2CCOCCO | CS[c:14]1[n:13][cH:12][n:11][c:10]2[cH:9][n:8][n:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][O:1]C(=O)c3ccccc3)[c:32]21.[NH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][c:26]([F:27])[cH:28]2)[c:29]([Cl:30])[cH:31]1>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][n:7]1[n:8][cH:9][c:10]2[n:11][cH:12][n:13... | CSc1ncnc2cnn(CCOCCOC(=O)c3ccccc3)c12.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | OCCOCCn1ncc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | b991550f9881431af8cd4a60ac672fac99dca6fecbceca0d6862dbad99c2772a | f34222d39fdeea750467d37a1cd0fc6ffe2b24879afdea2beeb808cc6f9a701e | c1ccc(COc2ccc(Nc3ncnc4cn[nH]c34)cc2)cc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[#7;a:8](-[C:9]):[c:10]:2:1.O=C(-[O;H0;D2;+0:11]-[C:12]-[C:13])-c1:c:c:c:c:c:1.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[C:9]-[#7;a:8]1:[#7;a:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17]):[c:10]:1:2.[C:13]-[C... | 30.6 | [{"value": 30.6, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=NN2CCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 16.5 | HOUR | A mixture of 2-{2-[7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]ethoxy}ethyl benzoate (200 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (140 mg), pyridine hydrochloride (96 mg) and 1-methyl-2-pyrrolidone (5 mL) was stirred at 140° C. for 16.5 hrs. The reaction mixture was poured into saturated aqueous sodium hydroge... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Monosulfide | Primary alcohol.Secondary amine | c1ncnc2c[nH]nc12.c1ccccc1 | c1ncnc2cn[nH]c12 | c1ncnc2cn[nH]c12.c1ccccc1.c1ccccc1 | Other | CN1C(CCC1)=O | 140 | 16.5 | CSc1ncnc2cnn(CCOCCOC(=O)c3ccccc3)c12.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>CN1C(CCC1)=O>OCCOCCn1ncc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-adbf14de9d254ecf88fe42752e99164e | CSc1ncnc2cnn(CCOCCOC(=O)c3ccccc3)c12.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>>OCCOCCn1ncc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | C(O)([O-])=O.[Na+].C(C1=CC=CC=C1)(=O)OCCOCCN1N=CC=2N=CN=C(C21)SC.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)C(F)(F)F.Cl.N1=CC=CC=C1>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=NN2CCOCCO | CS[c:14]1[n:13][cH:12][n:11][c:10]2[cH:9][n:8][n:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][O:1]C(=O)c3ccccc3)[c:34]21.[NH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]2)[c:31]([Cl:32])[cH:33]1>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][n:7]1[n:8][cH:9][c:10]2[n:1... | CSc1ncnc2cnn(CCOCCOC(=O)c3ccccc3)c12.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1 | OCCOCCn1ncc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | b991550f9881431af8cd4a60ac672fac99dca6fecbceca0d6862dbad99c2772a | f34222d39fdeea750467d37a1cd0fc6ffe2b24879afdea2beeb808cc6f9a701e | c1ccc(Oc2ccc(Nc3ncnc4cn[nH]c34)cc2)cc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[#7;a:8](-[C:9]):[c:10]:2:1.O=C(-[O;H0;D2;+0:11]-[C:12]-[C:13])-c1:c:c:c:c:c:1.[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[C:9]-[#7;a:8]1:[#7;a:7]:[c:6]:[c:5]2:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17]):[c:10]:1:2.[C:13]-[C... | 11.1 | [{"value": 11.1, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=NN2CCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 33.5 | HOUR | A mixture of 2-{2-[7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidin-1-yl]ethoxy}ethyl benzoate (328 mg), 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (264 mg), pyridine hydrochloride (159 mg) and 1-methyl-2-pyrrolidone (7.5 mL) was stirred at 140° C. for 33.5 hrs. The reaction mixture was poured into saturated aqueous sodi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Monosulfide | Primary alcohol.Secondary amine | c1ncnc2c[nH]nc12.c1ccccc1 | c1ncnc2cn[nH]c12 | c1ncnc2cn[nH]c12.c1ccccc1.c1ccccc1 | Other | CN1C(CCC1)=O | 140 | 33.5 | CSc1ncnc2cnn(CCOCCOC(=O)c3ccccc3)c12.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>CN1C(CCC1)=O>OCCOCCn1ncc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dac612e5b1094d8cb4d10e4b5dcb4f11 | Nc1c(I)ncnc1Oc1ccccc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CC#Cc1ncnc(Oc2ccccc2)c1N | IC1=NC=NC(=C1N)OC1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[F-].[K+].C(O)([O-])=O.[Na+]>>O(C1=CC=CC=C1)C1=NC=NC(=C1N)C#CC | I[c:4]1[n:5][cH:6][n:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]1[NH2:17].c1ccc(P(c2ccccc2)c2cc[cH:2][cH:1]c2)cc1>>[CH3:1][C:2]#[C:3][c:4]1[n:5][cH:6][n:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]1[NH2:17] | Nc1c(I)ncnc1Oc1ccccc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | CC#Cc1ncnc(Oc2ccccc2)c1N | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C[Si](C#CC)(C)C.C(C)N(CC)CC.CN(C=O)C | C-C Coupling | OtherReaction | c70aac20f1e8fff2430b346316c43ec62095590cec421b29bf0050c478d937e0 | 1e016b25438ccc05198b60acd46c3be4f5258f827b14753e63a4bafcf188d801 | c1ccc(Oc2ccncn2)cc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#8:6]):[c:7]:1-[N;D1;H2:8].[cH;D2;+0:9]1:[cH;D2;+0:10]:c:c:c(-P(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2):c:1>>[#8:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C:11]#[C;H0;D2;+0:10]-[CH3;D1;+0:9]):[c:7]:1-[N;D1;H2:8] | 730 | [{"value": 730.0, "product": "O(C1=CC=CC=C1)C1=NC=NC(=C1N)C#CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 16 | HOUR | 4-Iodo-6-phenoxypyrimidin-5-amine (5.00 g) was dissolved in a mixed solvent of N,N-dimethylformamide (100 mL)/triethylamine (50 mL), and 1-(trimethylsilyl)-1-propyne (3.3 mL), trans-dichlorobis(triphenylphosphine)palladium(II) (557.7 mg), triphenylphosphine (421.1 mg), copper(I) iodide (303.0 mg) and potassium fluoride... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Alkyne | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C[Si](C#CC)(C)C.C(C)N(CC)CC.CN(C=O)C | 60 | 16 | Nc1c(I)ncnc1Oc1ccccc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C[Si](C#CC)(C)C.C(C)N(CC)CC.CN(C=O)C>CC#Cc1ncnc(Oc2ccccc2)c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-761d2778fbd049bab6f85c1e6557ac82 | CC#Cc1ncnc(Oc2ccccc2)c1N>>Cc1cc2ncnc(Oc3ccccc3)c2[nH]1 | O.CC(C)([O-])C.[K+].O(C1=CC=CC=C1)C1=NC=NC(=C1N)C#CC>>CC1=CC=2N=CN=C(C2N1)OC1=CC=CC=C1 | [CH3:1][C:2]#[C:3][c:4]1[n:5][cH:6][n:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]1[NH2:17]>>[CH3:1][c:2]1[cH:3][c:4]2[n:5][cH:6][n:7][c:8]([O:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16]2[nH:17]1 | CC#Cc1ncnc(Oc2ccccc2)c1N | Cc1cc2ncnc(Oc3ccccc3)c2[nH]1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 4074b4d15ae59e43a9db38b88971d3da4bc2c5011d6f413a05bb8fbb5a5c4621 | f32b9a5ecc70d866a53cd56f9bc47b365771cdcbb02563cae8c78e4de228d870 | c1ccc(Oc2ncnc3cc[nH]c23)cc1 | [#8:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[C;H0;D2;+0:7]#[C;H0;D2;+0:8]-[C;D1;H3:9]):[c:10]:1-[NH2;D1;+0:11]>>[#8:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C;D1;H3:9]):[nH;D2;+0:11]:[c:10]:2:1 | 74.6 | [{"value": 74.6, "product": "CC1=CC=2N=CN=C(C2N1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | 4-Phenoxy-6-prop-1-yn-1-ylpyrimidin-5-amine (776.0 mg) was dissolved in tetrahydrofuran (30 mL) and cooled to 0° C. To this solution was added dropwise a 1.0 M solution (4 mL) of potassium tert-butoxide in tetrahydrofuran, and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Alkyne | null | c1cncnc1 | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1.c1ccccc1 | null | O1CCCC1 | 0 | 0.5 | CC#Cc1ncnc(Oc2ccccc2)c1N>O1CCCC1>Cc1cc2ncnc(Oc3ccccc3)c2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ee71dde949f4f358ce291d56e2f03a0 | CS(=O)(=O)OCCOCCOC(=O)c1ccccc1.Cc1cc2ncnc(Oc3ccccc3)c2[nH]1>>Cc1cc2ncnc(Oc3ccccc3)c2n1CCOCCOC(=O)c1ccccc1 | O.CC1=CC=2N=CN=C(C2N1)OC1=CC=CC=C1.C(C1=CC=CC=C1)(=O)OCCOCCOS(=O)(=O)C.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)(=O)OCCOCCN1C(=CC=2N=CN=C(C21)OC2=CC=CC=C2)C | CS(=O)(=O)O[CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][C:24](=[O:25])[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1.[CH3:1][c:2]1[cH:3][c:4]2[n:5][cH:6][n:7][c:8]([O:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16]2[nH:17]1>>[CH3:1][c:2]1[cH:3][c:4]2[n:5][cH:6][n:7][c:8]([O:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15... | CS(=O)(=O)OCCOCCOC(=O)c1ccccc1.Cc1cc2ncnc(Oc3ccccc3)c2[nH]1 | Cc1cc2ncnc(Oc3ccccc3)c2n1CCOCCOC(=O)c1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 799693fcd64290548f5b8fe439270e11c4e66a00fcafd8d3130b01104a0a94d8 | 0b4f3c8c88df0a792d0db7d59004d7fe5681a61dd48ef2449ddca2d636f76ada | O=C(OCCOCCn1ccc2ncnc(Oc3ccccc3)c21)c1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#8:3].[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11](-[C;D1;H3:12]):[nH;D2;+0:13]:[c:14]:2:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:14]2:[c:9](:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:2-[#8:4]):[c:10]:[c:11]:1-[C;D1;H3:12] | 93.2 | [{"value": 93.2, "product": "C(C1=CC=CC=C1)(=O)OCCOCCN1C(=CC=2N=CN=C(C21)OC2=CC=CC=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 21 | HOUR | 6-Methyl-4-phenoxy-5H-pyrrolo[3,2-d]pyrimidine (299.9 mg) and 2-{2-[(methylsulfonyl)oxy]ethoxy}ethyl benzoate (464.1 mg) were dissolved in N,N-dimethylformamide (7 mL), potassium carbonate (431 mg) was added, and the mixture was stirred at 60° C. for 21 hr. Water was added to the reaction mixture, and the mixture was e... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1ncc2[nH]ccc2n1 | c1cc2ncncc2[nH]1 | c1cc2ncncc2[nH]1.c1ccccc1.c1ccccc1 | MsOH.HO- | CN(C=O)C | 60 | 21 | CS(=O)(=O)OCCOCCOC(=O)c1ccccc1.Cc1cc2ncnc(Oc3ccccc3)c2[nH]1>CN(C=O)C>Cc1cc2ncnc(Oc3ccccc3)c2n1CCOCCOC(=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36518e2fb4b6466a9fb8c604a8f7725d | Cc1cc2ncnc(Oc3ccccc3)c2n1CCOCCOC(=O)c1ccccc1.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>>Cc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1CCOCCOC(=O)c1ccccc1 | Cl.N1=CC=CC=C1.C1(=CC=CC=C1)O.C(C1=CC=CC=C1)(=O)OCCOCCN1C(=CC=2N=CN=C(C21)OC2=CC=CC=C2)C.ClC=1C=C(N)C=CC1OCC1=CC(=CC=C1)F.Cl.N1=CC=CC=C1.C1(=CC=CC=C1)O>>C(C1=CC=CC=C1)(=O)OCCOCCN1C(=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OCC2=CC(=CC=C2)F)Cl)C | c1ccc(O[c:8]2[n:7][cH:6][n:5][c:4]3[cH:3][c:2]([CH3:1])[n:27]([CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][C:34](=[O:35])[c:36]4[cH:37][cH:38][cH:39][cH:40][cH:41]4)[c:26]32)cc1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][c:20]([F:21])[cH:22]2)[c:23]([Cl:24])[cH:25]1>>[CH3:1][c:2]1[cH:... | Cc1cc2ncnc(Oc3ccccc3)c2n1CCOCCOC(=O)c1ccccc1.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1 | Cc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1CCOCCOC(=O)c1ccccc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Displacement of ethoxy group by primary amine | 4576865c4963154207b2712e5437aabbb5a2007c337967bf6fa29599f0015795 | 953ca34981f329c845365ec5b25a3d27fa72aebd3e467f4e6ef8becba38a9d76 | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c21)c1ccccc1 | [C:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-O-c3:c:c:c:c:c:3):[c:10]:1:2.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:10]:1:2 | 26.2 | [{"value": 26.2, "product": "C(C1=CC=CC=C1)(=O)OCCOCCN1C(=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OCC2=CC(=CC=C2)F)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 3 | HOUR | A mixture of 2-[2-(6-methyl-4-phenoxy-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy]ethyl benzoate (92.3 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (86.3 mg), pyridine hydrochloride (81.6 mg) and phenol (156.1 mg) was stirred at 120° C. for 3 hrs, and at 140° C. for 5.5 hrs. Further, pyridine hydrochloride (77.6 mg) and phe... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary amine | c1ccccc1.c1cc2ncncc2[nH]1 | c1cc2ncncc2[nH]1 | c1cc2ncncc2[nH]1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | ClCCl | 120 | 3 | Cc1cc2ncnc(Oc3ccccc3)c2n1CCOCCOC(=O)c1ccccc1.Nc1ccc(OCc2cccc(F)c2)c(Cl)c1>ClCCl>Cc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1CCOCCOC(=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d10cc918c728473fb07bd6ccf68b0549 | Cc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1CCOCCOC(=O)c1ccccc1>>Cc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1CCOCCO | C(C1=CC=CC=C1)(=O)OCCOCCN1C(=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OCC2=CC(=CC=C2)F)Cl)C.[OH-].[Na+].Cl>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2CCOCCO)C | O=C(c1ccccc1)[O:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][n:27]1[c:2]([CH3:1])[cH:3][c:4]2[n:5][cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]4[cH:17][cH:18][cH:19][c:20]([F:21])[cH:22]4)[c:23]([Cl:24])[cH:25]3)[c:26]21>>[CH3:1][c:2]1[cH:3][c:4]2[n:5][cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][... | Cc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1CCOCCOC(=O)c1ccccc1 | Cc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1CCOCCO | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 8df1b5c4ec88eb8f4e334a9ade2ac7fc0b3f460ea1450816d1758f28eee39662 | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O=C(-[O;H0;D2;+0:1]-[C:2]-[C:3])-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[OH;D1;+0:1] | 59.6 | [{"value": 59.6, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC=1C2=C(N=CN1)C=C(N2CCOCCO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 2-{2-[4-({3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethoxy}ethyl benzoate (90.0 mg) was dissolved in methanol (1 mL), 1N aqueous sodium hydroxide solution (0.3 mL) was added, and the mixture was stirred at room temperature for 5 hrs. The reaction mixture was neutralized with... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | c1ccccc1 | null | c1cc2ncncc2[nH]1.c1ccccc1.c1ccccc1 | HO- | CO | null | 5 | Cc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1CCOCCOC(=O)c1ccccc1>CO>Cc1cc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2n1CCOCCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2538e21d79e144199f66b16900906621 | CCOC(C#Cc1ncnc(Oc2ccccc2)c1N)OCC>>CCOC(OCC)c1cc2ncnc(Oc3ccccc3)c2[nH]1 | C(C)OC(C#CC1=NC=NC(=C1N)OC1=CC=CC=C1)OCC.CC(C)([O-])C.[K+].O>>C(C)OC(C1=CC=2N=CN=C(C2N1)OC1=CC=CC=C1)OCC | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C:8]#[C:9][c:10]1[n:11][cH:12][n:13][c:14]([O:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]1[NH2:23]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[c:8]1[cH:9][c:10]2[n:11][cH:12][n:13][c:14]([O:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[c:22]2[nH:23]1 | CCOC(C#Cc1ncnc(Oc2ccccc2)c1N)OCC | CCOC(OCC)c1cc2ncnc(Oc3ccccc3)c2[nH]1 | null | null | O1CCCC1.CN1C(CCC1)=O | Aromatic Heterocycle Formation | OtherReaction | 4074b4d15ae59e43a9db38b88971d3da4bc2c5011d6f413a05bb8fbb5a5c4621 | f32b9a5ecc70d866a53cd56f9bc47b365771cdcbb02563cae8c78e4de228d870 | c1ccc(Oc2ncnc3cc[nH]c23)cc1 | [#8:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[C;H0;D2;+0:7]#[C;H0;D2;+0:8]-[C:9](-[#8:10])-[#8:11]):[c:12]:1-[NH2;D1;+0:13]>>[#8:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C:9](-[#8:10])-[#8:11]):[nH;D2;+0:13]:[c:12]:2:1 | 58.3 | [{"value": 58.3, "product": "C(C)OC(C1=CC=2N=CN=C(C2N1)OC1=CC=CC=C1)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | 4-(3,3-Diethoxyprop-1-yn-1-yl)-6-phenoxypyrimidin-5-amine (2.30 g) was dissolved in 1-methyl-2-pyrrolidone (7.5 mL), and the mixture was cooled to 0° C. A solution (7.6 mL) of potassium tert-butoxide in 1.0 M tetrahydrofuran was added dropwise to this solution, and the mixture was stirred at 0° C. for 30 min. and at ro... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Alkyne | null | c1cncnc1 | c1ncc2[nH]ccc2n1 | c1ncc2[nH]ccc2n1.c1ccccc1 | null | O1CCCC1.CN1C(CCC1)=O | 0 | 1.5 | CCOC(C#Cc1ncnc(Oc2ccccc2)c1N)OCC>O1CCCC1.CN1C(CCC1)=O>CCOC(OCC)c1cc2ncnc(Oc3ccccc3)c2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8adceef9c7d44a198d276a70cf3cca72 | CCOC(OCC)c1cc2ncnc(Oc3ccccc3)c2[nH]1>>O=Cc1cc2ncnc(Oc3ccccc3)c2[nH]1 | C(C)OC(C1=CC=2N=CN=C(C2N1)OC1=CC=CC=C1)OCC.Cl.[OH-].[Na+]>>O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=C(N2)C=O | CCO[CH:2]([O:1]CC)[c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([O:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17]2[nH:18]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([O:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17]2[nH:18]1 | CCOC(OCC)c1cc2ncnc(Oc3ccccc3)c2[nH]1 | O=Cc1cc2ncnc(Oc3ccccc3)c2[nH]1 | null | null | O1CCCC1 | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccc(Oc2ncnc3cc[nH]c23)cc1 | C-C-O-[CH;D3;+0:1](-[O;H0;D2;+0:2]-C-C)-[c:3]1:[#7;a:4]:[c:5](:[c:6]:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:1>>[#7;a:9]:[c:8]1:[c:10]:[c:3](-[CH;D2;+0:1]=[O;H0;D1;+0:2]):[#7;a:4]:[c:5]:1:[c:6]:[#7;a:7] | 90.2 | [{"value": 90.2, "product": "O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=C(N2)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 6-(Diethoxymethyl)-4-phenoxy-5H-pyrrolo[3,2-d]pyrimidine (3.15 g) was dissolved in tetrahydrofuran (40 mL), 1N hydrochloric acid (40 mL) was added, and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was neutralized with 1N aqueous sodium hydroxide solution, and extracted with a mixed solven... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ncc2[nH]ccc2n1.c1ccccc1 | HO- | O1CCCC1 | null | 2 | CCOC(OCC)c1cc2ncnc(Oc3ccccc3)c2[nH]1>O1CCCC1>O=Cc1cc2ncnc(Oc3ccccc3)c2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-110e71ba28f844ce97d0137cbb260e08 | O=Cc1cc2ncnc(Oc3ccccc3)c2[nH]1>>O=C(O)c1cc2ncnc(Oc3ccccc3)c2[nH]1 | C(O)([O-])=O.[Na+].P(=O)(O)(O)[O-].[Na+].O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=C(N2)C=O.Cl(=O)[O-].[Na+].Cl>>O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=C(N2)C(=O)O | [O:1]=[CH:2][c:4]1[cH:5][c:6]2[n:7][cH:8][n:9][c:10]([O:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18]2[nH:19]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]2[n:7][cH:8][n:9][c:10]([O:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18]2[nH:19]1 | O=Cc1cc2ncnc(Oc3ccccc3)c2[nH]1 | O=C(O)c1cc2ncnc(Oc3ccccc3)c2[nH]1 | null | null | O.CS(=O)C | Oxidation | Oxidation of aldehydes to carboxylic acids | 53d556378d4cb30c33d50a2e1886f8fba4abcbb7065d1faceeb5e5968b58008d | 2f35b69536247c389825da7241226b4e568110d1cfe736c83136d58ad1c9dae2 | c1ccc(Oc2ncnc3cc[nH]c23)cc1 | [#7;a:1]:[c:2]1:[c:3]:[c:4](-[CH;D2;+0:5]=[O;D1;H0:6]):[#7;a:7]:[c:8]:1:[c:9]:[#7;a:10]>>[#7;a:1]:[c:2]1:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;D1;H1:11]):[#7;a:7]:[c:8]:1:[c:9]:[#7;a:10] | 103.7 | [{"value": 103.7, "product": "O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=C(N2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 4-Phenoxy-5H-pyrrolo[3,2-d]pyrimidine-6-carbaldehyde (2.17 g) was dissolved in dimethyl sulfoxide (21 mL) and a solution of sodium dihydrogen phosphate (5.45 g) in water (14 mL) was added. A solution of sodium chlorite (2.06 g) in water (14 mL) was added dropwise to this solution, and the mixture was stirred for 2 hrs.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid | null | null | c1ncc2[nH]ccc2n1.c1ccccc1 | Other | O.CS(=O)C | null | 2 | O=Cc1cc2ncnc(Oc3ccccc3)c2[nH]1>O.CS(=O)C>O=C(O)c1cc2ncnc(Oc3ccccc3)c2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f8ac4050ac0942b3a95d6783bc28672a | NC(=O)c1cc2ncnc(Oc3ccccc3)c2[nH]1>>N#Cc1cc2ncnc(Oc3ccccc3)c2[nH]1 | O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=C(N2)C(=O)N>>O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=C(N2)C#N | O=[C:2]([NH2:1])[c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([O:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17]2[nH:18]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([O:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17]2[nH:18]1 | NC(=O)c1cc2ncnc(Oc3ccccc3)c2[nH]1 | N#Cc1cc2ncnc(Oc3ccccc3)c2[nH]1 | null | null | P(=O)(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | c1ccc(Oc2ncnc3cc[nH]c23)cc1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[c:3]1:[#7;a:4]:[c:5](:[c:6]:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:1>>[#7;a:9]:[c:8]1:[c:10]:[c:3](-[C;H0;D2;+0:1]#[N;H0;D1;+0:2]):[#7;a:4]:[c:5]:1:[c:6]:[#7;a:7] | 69 | [{"value": 69.0, "product": "O(C1=CC=CC=C1)C=1C2=C(N=CN1)C=C(N2)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 3 | HOUR | 4-Phenoxy-5H-pyrrolo[3,2-d]pyrimidine-6-carboxamide (1.67 g) was suspended in phosphorus oxychloride (20 mL), and the suspension was stirred at 70° C. for 3 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in tetrahydrofuran (25 mL). Water and aqueous ammonia were added t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ncc2[nH]ccc2n1.c1ccccc1 | HO- | P(=O)(Cl)(Cl)Cl | 70 | 3 | NC(=O)c1cc2ncnc(Oc3ccccc3)c2[nH]1>P(=O)(Cl)(Cl)Cl>N#Cc1cc2ncnc(Oc3ccccc3)c2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d5c0c5798ac641e58e67cc63fe348832 | CS(=O)(=O)OCCCOCCOC1CCCCO1.Clc1ncnc2cc[nH]c12>>Clc1ncnc2ccn(CCCOCCOC3CCCCO3)c12 | O.ClC=1C2=C(N=CN1)C=CN2.CS(=O)(=O)OCCCOCCOC1OCCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>>ClC=1C2=C(N=CN1)C=CN2CCCOCCOC2OCCCC2 | CS(=O)(=O)O[CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][O:22]1.[Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][cH:8][nH:9][c:23]12>>[Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][cH:8][n:9]([CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][O:... | CS(=O)(=O)OCCCOCCOC1CCCCO1.Clc1ncnc2cc[nH]c12 | Clc1ncnc2ccn(CCCOCCOC3CCCCO3)c12 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 1c5a458f177d506b085e5db8a4d26fb6365a361ed15b678e58c1d38f12fc1d44 | 0b4f3c8c88df0a792d0db7d59004d7fe5681a61dd48ef2449ddca2d636f76ada | c1ncc2c(ccn2CCCOCCOC2CCCCO2)n1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[Cl;D1;H0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1:2>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5](-[Cl;D1;H0:4]):[c:13]:2:1 | 84.4 | [{"value": 84.4, "product": "ClC=1C2=C(N=CN1)C=CN2CCCOCCOC2OCCCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 4.5 | HOUR | 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (203.6 mg), 3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]propyl methanesulfonate (559.3 mg) was dissolved in N,N-dimethylformamide (4 mL), cesium carbonate (1.30 g) was added, and the mixture was stirred at 40° C. for 4.5 hrs. Water was added to the reaction mixture and the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.C1CCOCC1 | MsOH.HO- | CN(C=O)C | 40 | 4.5 | CS(=O)(=O)OCCCOCCOC1CCCCO1.Clc1ncnc2cc[nH]c12>CN(C=O)C>Clc1ncnc2ccn(CCCOCCOC3CCCCO3)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-451c826794d446c49ead31291ad47dc0 | Clc1ncnc2ccn(CCCOCCOC3CCCCO3)c12.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>>Cl.OCCOCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | ClC=1C2=C(N=CN1)C=CN2CCCOCCOC2OCCCC2.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)C(F)(F)F.C(O)([O-])=O.[Na+]>>Cl.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCCOCCO | C1CCC([O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][n:9]2[cH:10][cH:11][c:12]3[n:13][cH:14][n:15][c:16]([Cl:1])[c:36]23)OC1.[NH2:17][c:18]1[cH:19][cH:20][c:21]([O:22][c:23]2[cH:24][cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]2)[c:33]([Cl:34])[cH:35]1>>[ClH:1].[OH:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][n... | Clc1ncnc2ccn(CCCOCCOC3CCCCO3)c12.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1 | Cl.OCCOCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | a011897c9fb72e04ab998d55161a11d105f977221807d53d2965a43c027dd818 | 93d4c305c5e59cab9f06d293066f82b0f14d5550003628e8f87167f2c78f7b16 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | [C:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-[Cl;H0;D1;+0:10]):[c:11]:1:2.[C:12]-[C:13]-[O;H0;D2;+0:14]-C1-C-C-C-C-O-1.[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[C:1]-[#7;a:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18]):[c:11]:1:2.[C:12]-[... | 65.5 | [{"value": 65.5, "product": "Cl.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 18 | HOUR | 4-Chloro-5-{3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]propyl}-5H-pyrrolo[3,2-d]pyrimidine (380.2 mg) was dissolved in isopropyl alcohol (7 mL), 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (419.2 mg) was added, and the mixture was stirred at 80° C. for 18 hrs. Saturated aqueous sodium hydrogen carbonate solution was a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Primary amine | Primary alcohol.Secondary amine | C1CCOCC1.c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | C(C)(C)O | 80 | 18 | Clc1ncnc2ccn(CCCOCCOC3CCCCO3)c12.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>C(C)(C)O>Cl.OCCOCCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5a68cff6e0a949568d05e21eb1ba7e22 | CCOC(=O)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>O=C(O)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | C(C)OC(CN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl)=O.Cl>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CC(=O)O | CC[O:3][C:2](=[O:1])[CH2:4][n:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]([O:18][c:19]4[cH:20][cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28]4)[c:29]([Cl:30])[cH:31]3)[c:32]12>>[O:1]=[C:2]([OH:3])[CH2:4][n:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11][c:12]([NH:13][c:14]3[cH:15]... | CCOC(=O)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | O=C(O)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O1CCCC1.[OH-].[Na+].C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 81.4 | [{"value": 81.4, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Ethyl[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]acetate (221.2 mg) was dissolved in a mixed solvent of tetrahydrofuran (1.5 mL)/ethanol (1.5 mL), 1N aqueous sodium hydroxide solution (0.6 mL) was added, and the mixture was stirred at room temperature for 30 min. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | Other | O1CCCC1.[OH-].[Na+].C(C)O | null | 0.5 | CCOC(=O)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>O1CCCC1.[OH-].[Na+].C(C)O>O=C(O)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f0ccf5a1222842219efd078042b691e6 | CS(=O)(=O)CCN.O=C(O)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CS(=O)(=O)CCNC(=O)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CS(=O)(=O)CCN.N1(N=NC2=C1C=CC=C2)O.Cl.CN(CCCN=C=NCC)C.CS(=O)(=O)CCN.N1(N=NC2=C1C=CC=C2)O.Cl.CN(CCCN=C=NCC)C.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CC(=O)O>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CC(=O)NCCS(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][NH2:7].O[C:8](=[O:9])[CH2:10][n:11]1[cH:12][cH:13][c:14]2[n:15][cH:16][n:17][c:18]([NH:19][c:20]3[cH:21][cH:22][c:23]([O:24][c:25]4[cH:26][cH:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34]4)[c:35]([Cl:36])[cH:37]3)[c:38]12>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][NH:... | CS(=O)(=O)CCN.O=C(O)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CS(=O)(=O)CCNC(=O)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O.C(C)N(CC)CC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 11.1 | [{"value": 11.1, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CC(=O)NCCS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | [4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]acetic acid (149.3 mg) was dissolved in N,N-dimethylformamide (1.6 mL), 2-(methylsulfonyl)ethanamine (60.3 mg), 1H-1,2,3-benzotriazol-1-ol (67.8 mg), triethylamine (0.15 mL) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hyd... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O.C(C)N(CC)CC.CN(C=O)C | null | 17 | CS(=O)(=O)CCN.O=C(O)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>O.C(C)N(CC)CC.CN(C=O)C>CS(=O)(=O)CCNC(=O)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13c303e5b3654a69bd4788d1e5a3b78e | CC(C)(C)[Si](C)(C)Cl.OCC#CCO>>CC(C)(C)[Si](C)(C)OCC#CCO | O.[H-].[Na+].C(C#CCO)O.[Si](C)(C)(C(C)(C)C)Cl>>[Si](C)(C)(C(C)(C)C)OCC#CCO | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][C:10]#[C:11][CH2:12][OH:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][C:10]#[C:11][CH2:12][OH:13] | CC(C)(C)[Si](C)(C)Cl.OCC#CCO | CC(C)(C)[Si](C)(C)OCC#CCO | null | null | O1CCCC1 | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]#[C:10]-[C:11]-[OH;D1;+0:12]>>[C:8]-[C:9]#[C:10]-[C:11]-[O;H0;D2;+0:12]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 21.2 | [{"value": 21.2, "product": "[Si](C)(C)(C(C)(C)C)OCC#CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 60% Sodium hydride (1.39 g) was suspended in tetrahydrofuran (50 mL), and the suspension was cooled to 0° C., a solution of but-2-yne-1,4-diol (3.0 g) in tetrahydrofuran (20 mL) was added dropwise, and the mixture was stirred at room temperature for 1 hr. tert-Butyldimethylsilyl chloride (5.26 g) was added to the react... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | null | HCl | O1CCCC1 | 0 | 1 | CC(C)(C)[Si](C)(C)Cl.OCC#CCO>O1CCCC1>CC(C)(C)[Si](C)(C)OCC#CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97fdc0d1badf4abf9f03a19ef5dd38f2 | CC(C)(C)[Si](C)(C)OCC#CCO.CS(=O)(=O)Cl>>CC(C)(C)[Si](C)(C)OCC#CCOS(C)(=O)=O | O.C(C)N(CC)CC.CS(=O)(=O)Cl.[Si](C)(C)(C(C)(C)C)OCC#CCO>>CS(=O)(=O)OCC#CCO[Si](C)(C)C(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][C:10]#[C:11][CH2:12][OH:13].Cl[S:14]([CH3:15])(=[O:16])=[O:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][C:10]#[C:11][CH2:12][O:13][S:14]([CH3:15])(=[O:16])=[O:17] | CC(C)(C)[Si](C)(C)OCC#CCO.CS(=O)(=O)Cl | CC(C)(C)[Si](C)(C)OCC#CCOS(C)(=O)=O | null | null | C(C)(=O)OCC | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]#[C:7]-[C:8]-[OH;D1;+0:9]>>[C:5]-[C:6]#[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | 0 | CELSIUS | 3 | HOUR | 4-{[Tert-butyl(dimethyl)silyl]oxy}but-2-yn-1-ol (701.4 mg) was dissolved in ethyl acetate (15 mL), and the solution was cooled to 0° C. Triethylamine (1.1 mL) and methanesulfonyl chloride (0.3 mL) were added, and the mixture was stirred at 0° C. for 3 hrs. Water was added to the reaction mixture and the mixture was ext... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | C(C)(=O)OCC | 0 | 3 | CC(C)(C)[Si](C)(C)OCC#CCO.CS(=O)(=O)Cl>C(C)(=O)OCC>CC(C)(C)[Si](C)(C)OCC#CCOS(C)(=O)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bfd3ab9b54804d81a3cff037051f5e76 | CC(C)(C)[Si](C)(C)OCC#CCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>>OCC#CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | [Si](C)(C)(C(C)(C)C)OCC#CCN1C=CC=2N=CN=C(C21)Cl.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)C(F)(F)F.O>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CC#CCO | CC(C)(C)[Si](C)(C)[O:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13](Cl)[c:33]12.[NH2:14][c:15]1[cH:16][cH:17][c:18]([O:19][c:20]2[cH:21][cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29]2)[c:30]([Cl:31])[cH:32]1>>[OH:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n... | CC(C)(C)[Si](C)(C)OCC#CCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1 | OCC#CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | b624bc9704f2c377e5645bf04556e06bb752979a7a57757ccb28b7528dba7cdb | d337dcc4d45d76994b602bcd9efe488c21f548918fbf873db58b4529a5769a6f | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]#[C:4]-[C:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9]2:[#7;a:10]:[c:11]:[#7;a:12]:[c;H0;D3;+0:13](-Cl):[c:14]:1:2.[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[OH;D1;+0:1]-[C:2]-[C:3]#[C:4]-[C:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9]2:[#7;a:10]:[c:11]:[#7;a:12]:[c;H0;D3;+0:13](-[NH;D2;+0:15]-[c:16... | 73.9 | [{"value": 73.9, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CC#CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 6 | HOUR | 5-(4-{[Tert-butyl(dimethyl)silyl]oxy}but-2-yn-1-yl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidine (408.3 mg) was dissolved in isopropyl alcohol (7 mL), 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (421.0 mg) was added, and the mixture was stirred at 80° C. for 6 hrs. Water was added to the reaction mixture and the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.TMS ether protective group | Primary alcohol.Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(C)(C)O | 80 | 6 | CC(C)(C)[Si](C)(C)OCC#CCn1ccc2ncnc(Cl)c21.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>C(C)(C)O>OCC#CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e335dea5f614c4dbccfe0386b8511db | OCC#CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>OC/C=C/Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | [H-].COCCO[Al+]OCCOC.[Na+].[H-].ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CC#CCO.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2C/C=C/CO | [OH:1][CH2:2][C:3]#[C:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([NH:14][c:15]3[cH:16][cH:17][c:18]([O:19][c:20]4[cH:21][cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29]4)[c:30]([Cl:31])[cH:32]3)[c:33]12>>[OH:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5][n:6]1[cH:7][cH:8][c:9]2[n:10][cH:11][n:12][c:13]([NH:14... | OCC#CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | OC/C=C/Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O1CCCC1.C1(=CC=CC=C1)C | Reduction | Hydrogenation (triple to double) | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | [#7;a:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[C:5]-[O;D1;H1:6]>>[#7;a:1]-[C:2]/[CH;D2;+0:3]=[CH;D2;+0:4]/[C:5]-[O;D1;H1:6] | 74.3 | [{"value": 74.3, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2C/C=C/CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | 70% Sodium bis(2-methoxyethoxy)aluminum hydride in toluene solution (0.8 mL) was dissolved in tetrahydrofuran (4 mL), and the solution was cooled to 0° C. A solution of 4-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]but-2-yn-1-ol (262.4 mg) in tetrahydrofuran (10 mL) was add... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | null | O1CCCC1.C1(=CC=CC=C1)C | 0 | 2 | OCC#CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>O1CCCC1.C1(=CC=CC=C1)C>OC/C=C/Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
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