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-15d9dcd887d94a9aa3a4e3d1faabafd1 | Clc1ncnc2cc[nH]c12.O=C(OCC(CBr)OC(=O)c1ccccc1)c1ccccc1>>O=C(OCC(Cn1ccc2ncnc(Cl)c21)OC(=O)c1ccccc1)c1ccccc1 | ClC=1C2=C(N=CN1)C=CN2.C(C1=CC=CC=C1)(=O)OCC(CBr)OC(C1=CC=CC=C1)=O.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>>C(C1=CC=CC=C1)(=O)OCC(CN1C=CC=2N=CN=C(C21)Cl)OC(C2=CC=CC=C2)=O | [nH:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][c:14]([Cl:15])[c:16]12.Br[CH2:6][CH:5]([CH2:4][O:3][C:2](=[O:1])[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[O:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[O:1]=[C:2]([O:3][CH2:4][CH:5]([CH2:6][n:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][n:13][c:14]([Cl:15])[c:... | Clc1ncnc2cc[nH]c12.O=C(OCC(CBr)OC(=O)c1ccccc1)c1ccccc1 | O=C(OCC(Cn1ccc2ncnc(Cl)c21)OC(=O)c1ccccc1)c1ccccc1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C(OCC(Cn1ccc2ncncc21)OC(=O)c1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[#8:4]-[C:5]=[O;D1;H0:6].[Cl;D1;H0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]2:[c:13]:[c:14]:[nH;D2;+0:15]:[c:16]:2:1>>[C:3]-[C:2](-[#8:4]-[C:5]=[O;D1;H0:6])-[CH2;D2;+0:1]-[n;H0;D3;+0:15]1:[c:14]:[c:13]:[c:12]2:[#7;a:11]:[c:10]:[#7;a:9]:[c:8](-[Cl;D1;H0:7]):[c:16]:2:1 | 28.3 | [{"value": 28.3, "product": "C(C1=CC=CC=C1)(=O)OCC(CN1C=CC=2N=CN=C(C21)Cl)OC(C2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 4 | HOUR | A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (500 mg), 3-bromopropane-1,2-diyl dibenzoate (1.77 g), cesium carbonate (1.59 g) and N,N-dimethylformamide (6.5 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (80 mL). The organic layer was separat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HBr | C(C)(=O)OCC | 80 | 4 | Clc1ncnc2cc[nH]c12.O=C(OCC(CBr)OC(=O)c1ccccc1)c1ccccc1>C(C)(=O)OCC>O=C(OCC(Cn1ccc2ncnc(Cl)c21)OC(=O)c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a8c24dac5c44e08bce93d42fbb68e1b | CN(C(=O)C(F)(F)F)c1c(I)ncnc1I.N#Cc1cccc(Oc2ccc(N)cc2Cl)c1>>CN(C(=O)C(F)(F)F)c1c(I)ncnc1Nc1ccc(Oc2cccc(C#N)c2)c(Cl)c1 | IC1=NC=NC(=C1N(C(C(F)(F)F)=O)C)I.NC1=CC(=C(OC=2C=C(C#N)C=CC2)C=C1)Cl.C(O)([O-])=O.[Na+]>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C#N)NC1=NC=NC(=C1N(C(C(F)(F)F)=O)C)I | I[c:15]1[c:9]([N:2]([CH3:1])[C:3](=[O:4])[C:5]([F:6])([F:7])[F:8])[c:10]([I:11])[n:12][cH:13][n:14]1.[NH2:16][c:17]1[cH:18][cH:19][c:20]([O:21][c:22]2[cH:23][cH:24][cH:25][c:26]([C:27]#[N:28])[cH:29]2)[c:30]([Cl:31])[cH:32]1>>[CH3:1][N:2]([C:3](=[O:4])[C:5]([F:6])([F:7])[F:8])[c:9]1[c:10]([I:11])[n:12][cH:13][n:14][c:1... | CN(C(=O)C(F)(F)F)c1c(I)ncnc1I.N#Cc1cccc(Oc2ccc(N)cc2Cl)c1 | CN(C(=O)C(F)(F)F)c1c(I)ncnc1Nc1ccc(Oc2cccc(C#N)c2)c(Cl)c1 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Oc2ccc(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-[#7:8]-[C:9]=[O;D1;H0:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[I;D1;H0:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:7]:1-[#7:8]-[C:9]=[O;D1;H0:10] | 44.3 | [{"value": 44.3, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C#N)NC1=NC=NC(=C1N(C(C(F)(F)F)=O)C)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | N-(4,6-Diiodopyrimidin-5-yl)-2,2,2-trifluoro-N-methylacetamide (3 g) and 3-(4-amino-2-chlorophenoxy)benzonitrile (1.69 g) were dissolved in 1-methyl-2-pyrrolidone (11.4 mL), and the mixture was stirred with heating at 100° C. for 16 hrs. To the reaction mixture was added aqueous sodium hydrogen carbonate (80 mL) and th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HI | CN1C(CCC1)=O | 100 | null | CN(C(=O)C(F)(F)F)c1c(I)ncnc1I.N#Cc1cccc(Oc2ccc(N)cc2Cl)c1>CN1C(CCC1)=O>CN(C(=O)C(F)(F)F)c1c(I)ncnc1Nc1ccc(Oc2cccc(C#N)c2)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ecf93b431f3f4e69b4a56b01fcadb82b | CN(C(=O)C(F)(F)F)c1c(I)ncnc1Nc1ccc(Oc2cccc(C#N)c2)c(Cl)c1>>CNc1c(I)ncnc1Nc1ccc(Oc2cccc(C#N)c2)c(Cl)c1 | C(C)(=O)OCC.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C#N)NC1=NC=NC(=C1N(C(C(F)(F)F)=O)C)I.[BH4-].[Na+]>>ClC1=C(OC=2C=C(C#N)C=CC2)C=CC(=C1)NC1=NC=NC(=C1NC)I | O=C(C(F)(F)F)[N:2]([CH3:1])[c:3]1[c:4]([I:5])[n:6][cH:7][n:8][c:9]1[NH:10][c:11]1[cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][cH:19][c:20]([C:21]#[N:22])[cH:23]2)[c:24]([Cl:25])[cH:26]1>>[CH3:1][NH:2][c:3]1[c:4]([I:5])[n:6][cH:7][n:8][c:9]1[NH:10][c:11]1[cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][cH:19][c:20](... | CN(C(=O)C(F)(F)F)c1c(I)ncnc1Nc1ccc(Oc2cccc(C#N)c2)c(Cl)c1 | CNc1c(I)ncnc1Nc1ccc(Oc2cccc(C#N)c2)c(Cl)c1 | null | null | C(C)(C)O.O1CCCC1 | Reduction | Hydrogenolysis of tertiary amines | 16961a3d99942c0ab361f2149cf4766848c112f4d4d9e5e515a20194fa44ecb0 | 9d0759623d33e2d41aafe1af3bb1025d4d7a88f20060c872279b889c110cab65 | c1ccc(Oc2ccc(Nc3ccncn3)cc2)cc1 | F-C(-F)(-F)-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[c:3]1:[c:4](-[I;D1;H0:5]):[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1-[#7:10]>>[#7:10]-[c:9]1:[#7;a:8]:[c:7]:[#7;a:6]:[c:4](-[I;D1;H0:5]):[c:3]:1-[NH;D2;+0:1]-[C;D1;H3:2] | 90.7 | [{"value": 90.7, "product": "ClC1=C(OC=2C=C(C#N)C=CC2)C=CC(=C1)NC1=NC=NC(=C1NC)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of N-(4-{[3-chloro-4-(3-cyanophenoxy)phenyl]amino}-6-iodopyrimidin-5-yl)-2,2,2-trifluoro-N-methylacetamide (1.0 g) in isopropanol-tetrahydrofuran (5.0 mL-10 mL) was added sodium borohydride (70 mg) at room temperature. The mixture was stirred at room temperature for 1.5 hrs, and ethyl acetate was added. T... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Tertiary amide | Secondary amine | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | Other | C(C)(C)O.O1CCCC1 | null | 1.5 | CN(C(=O)C(F)(F)F)c1c(I)ncnc1Nc1ccc(Oc2cccc(C#N)c2)c(Cl)c1>C(C)(C)O.O1CCCC1>CNc1c(I)ncnc1Nc1ccc(Oc2cccc(C#N)c2)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72c172c741374100bf28532885c01fb5 | COS(C)(=O)=O.Nc1c(I)ncnc1I>>CNc1c(I)ncnc1I | C(C)(=O)OCC.CS(=O)(=O)OC.IC1=NC=NC(=C1N)I.[H-].[Na+]>>IC1=NC=NC(=C1NC)I | CS(=O)(=O)O[CH3:1].[NH2:2][c:3]1[c:4]([I:5])[n:6][cH:7][n:8][c:9]1[I:10]>>[CH3:1][NH:2][c:3]1[c:4]([I:5])[n:6][cH:7][n:8][c:9]1[I:10] | COS(C)(=O)=O.Nc1c(I)ncnc1I | CNc1c(I)ncnc1I | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | c1cncnc1 | C-S(=O)(=O)-O-[CH3;D1;+0:1].[I;D1;H0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7](-[I;D1;H0:8]):[c:9]:1-[NH2;D1;+0:10]>>[CH3;D1;+0:1]-[NH;D2;+0:10]-[c:9]1:[c:7](-[I;D1;H0:8]):[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:1-[I;D1;H0:2] | null | [] | null | null | 30 | MINUTE | To a solution of 4,6-diiodopyrimidin-5-amine (1.0 g) in tetrahydrofuran (10 mL) was added sodium hydride (60%, 138 mg) under ice-cooling. The mixture was stirred at room temperature for 30 min. To the reaction system was added dropwise a solution of methyl methanesulfonate (0.256 mL) in tetrahydrofuran (4.0 mL). The mi... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | c1cncnc1 | MsOH.HO- | O1CCCC1 | null | 0.5 | COS(C)(=O)=O.Nc1c(I)ncnc1I>O1CCCC1>CNc1c(I)ncnc1I |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79d8f9174b804d84b1fa5b73fbf2f019 | CC(C)(CO)C(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CC(C)(CO)C(=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.OCC(C(=O)O)(C)C.Cl.C(C)N=C=NCCCN(C)C.O.ON1N=NC2=C1C=CC=C2>>Cl.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(C(CO)(C)C)=O | O[C:6]([C:2]([CH3:1])([CH3:3])[CH2:4][OH:5])=[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])([CH2:4][OH:5])[C:6](=[O... | CC(C)(CO)C(=O)O.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CC(C)(CO)C(=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;D1;H3:5])-[C;D1;H3:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[C;D1;H3:6] | 141.4 | [{"value": 141.4, "product": "Cl.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(C(CO)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | A solution 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-2,2-dimethylpropanoic acid (68 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (166 mg), 1-hydroxybenzotriazole monohydrate (132 mg) and triethylamine ... | 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 | 15 | CC(C)(CO)C(=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)(CO)C(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-65461c604e27486ea7313b751fc8862c | Cc1ccc(S(=O)(=O)O)cc1>>Cc1ccc(S(=O)(=O)O)cc1 | 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.CC1=CC=C(C=C1)S(=O)(=O)O>>CC1=CC=C(C=C1)S(=O)(=O)O.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CS(=O)(=O)C)=O | [CH3:39][c:40]1[cH:41][cH:42][c:43]([S:44](=[O:45])(=[O:46])[OH:47])[cH:48][cH:49]1>>[CH3:39][c:40]1[cH:41][cH:42][c:43]([S:44](=[O:45])(=[O:46])[OH:47])[cH:48][cH:49]1 | Cc1ccc(S(=O)(=O)O)cc1 | Cc1ccc(S(=O)(=O)O)cc1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | 76.9 | [{"value": 76.9, "product": "CC1=CC=C(C=C1)S(=O)(=O)O.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 | To a solution of N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-2-(methylsulfonyl)acetamide (150 mg) in ethyl acetate (10 mL) was added 4-methylbenzenesulfonic acid monohydrate (55.4 mg) at room temperature. The mixture was stirred at room temperature for 20 hrs, a... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(C)(=O)OCC | null | 20 | Cc1ccc(S(=O)(=O)O)cc1>C(C)(=O)OCC>Cc1ccc(S(=O)(=O)O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dbc2033accfe4a1fb1f00e519e28f15c | CC(Cn1ccc2ncnc(Cl)c21)NC(=O)OC(C)(C)C.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>>CC(N)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.Cl | C(=O)(OC(C)(C)C)OC(=O)OC(C)(C)C.C(C)(C)(C)OC(NC(CN1C=CC=2N=CN=C(C21)Cl)C)=O.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)C(F)(F)F.Cl>>Cl.Cl.NC(CN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl)C | CC(C)(C)OC(=O)[NH:3][CH:2]([CH3:1])[CH2:4][n:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11][c:12]([Cl:34])[c:32]12.[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>>[CH3:1][CH:2]([NH2:3])[CH2:4][n:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][n:11][... | CC(Cn1ccc2ncnc(Cl)c21)NC(=O)OC(C)(C)C.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1 | CC(N)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.Cl | null | null | O1CCCC1.O.C(C)N(CC)CC.CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | 52eabfea8525971db681e2ff459bf7eb578389257f19a2ae4aa6823100bd47a3 | b189e21881719932ff7e93d2cee73d5d9b679e27f974877dd5fa270130c3c7ff | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C:4]-[#7;a:5]1:[c:6]:[c:7]:[c:8]2:[#7;a:9]:[c:10]:[#7;a:11]:[c;H0;D3;+0:12](-[Cl;H0;D1;+0:13]):[c:14]:1:2.[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[C;D1;H3:3]-[C:2](-[NH2;D1;+0:1])-[C:4]-[#7;a:5]1:[c:6]:[c:7]:[c:8]2:[#7;a:9]:[c:10]:[#7;a:11]:[c;H0;D3;+0:12](-[NH;D2;+0... | 57.2 | [{"value": 57.2, "product": "Cl.Cl.NC(CN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A solution of tert-butyl[2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)-1-methylethyl]carbamate (350 mg) and 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (423 mg) in 1-methyl-2-pyrrolidone (3.5 mL) was stirred at 120° C. for 4 hrs. After cooling to room temperature, triethylamine (0.24 mL) and di-tert-butyl dicarbonate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Primary amine.Boc | Primary amine.Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | O1CCCC1.O.C(C)N(CC)CC.CN1C(CCC1)=O | null | 20 | CC(Cn1ccc2ncnc(Cl)c21)NC(=O)OC(C)(C)C.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>O1CCCC1.O.C(C)N(CC)CC.CN1C(CCC1)=O>CC(N)Cn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6b55629e401480eb9c9dd6f626fafe0 | CS(=O)(=O)O>>CS(=O)(=O)O | ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CC(C)(C)O)=O.CS(=O)(=O)O>>CS(=O)(=O)O.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CC(C)(C)O)=O | [CH3:39][S:40](=[O:41])(=[O:42])[OH:43]>>[CH3:39][S:40](=[O:41])(=[O:42])[OH:43] | CS(=O)(=O)O | CS(=O)(=O)O | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 1 | HOUR | To a solution of N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxy-3-methylbutanamide (200 mg) in ethyl acetate (10 mL) was added methanesulfonic acid (26 μL) at room temperature. The mixture was stirred at room temperature for 1 hr and concentrated under re... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(=O)OCC | null | 1 | CS(=O)(=O)O>C(C)(=O)OCC>CS(=O)(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-895c14f759f5434c80c0ce33d78542f9 | O=C1c2ccccc2C(=O)N1CCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CC(=O)NCCOCCn1ccc2ncnc(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=CN2CCOCCN2C(C1=CC=CC=C1C2=O)=O.O.NN.C(O)([O-])=O.[Na+]>>ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCCNC(C)=O | O=C1c2cccc[c:1]2[C:2](=[O:3])[N:4]1[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][C:2](=[O:3])[NH:4][CH2:5][CH2:6][O:7][CH2:... | O=C1c2ccccc2C(=O)N1CCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CC(=O)NCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(C)O | Reduction | OtherReaction | d9171dbb22691e73cd44616f21fa6dcc09b4c3cd8ebc10a38d0adf93000789a7 | 15328f7911cf420e5b98cd32bf65857f1b0cf0d0f9e28f1ac7b23b1642c85385 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:6]2:c:c:c:c:c:2-1>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4](-[CH3;D1;+0:6])=[O;D1;H0:5] | 85 | [{"value": 85.0, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCCNC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2-(2-{2-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethoxy}ethyl)-1H-isoindole-1,3(2H)-dione (200 mg) was dissolved in ethanol (5.0 mL), hydrazine monohydrate (3.0 mL) was added, and the mixture was stirred for 1 hr. To the reaction mixture was added saturated aqueous sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary amide | c1ccc2c(c1)C[NH]C2 | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | Other | C(C)O | null | 1 | O=C1c2ccccc2C(=O)N1CCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>C(C)O>CC(=O)NCCOCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d02c53dd9aa349dfa54725c51b49d7d6 | C=CC(=O)OCC.Clc1ncnc2cc[nH]c12>>CCOC(=O)CCn1ccc2ncnc(Cl)c21 | C(C=C)(=O)OCC.[Cl-].[NH4+].C(C=C)(=O)OCC.C([O-])([O-])=O.[K+].[K+].C(C=C)(=O)OCC.C([O-])([O-])=O.[K+].[K+].ClC=1C2=C(N=CN1)C=CN2>>ClC=1C2=C(N=CN1)C=CN2CCC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].[nH:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][n:14][c:15]([Cl:16])[c:17]12>>[CH3:1][CH2:2][O:3][C: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]([Cl:16])[c:17]12 | C=CC(=O)OCC.Clc1ncnc2cc[nH]c12 | CCOC(=O)CCn1ccc2ncnc(Cl)c21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4630ca5b1c48d0db9b828625c844c1c8a6e34988bffd712ddc4b008089593e34 | 51fad62e29f5f77e8a2cefce7ceeba2655475fda67fa72d63935019e1a813761 | c1ncc2[nH]ccc2n1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[Cl;D1;H0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]2:[c:13]:[c:14]:[nH;D2;+0:15]:[c:16]:2:1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[n;H0;D3;+0:15]1:[c:14]:[c:13]:[c:12]2:[#7;a:11]:[c:10]:[#7;a:9]:[c:8](-[Cl;D1;H0:7]):[c:16]:2:1 | null | [] | null | null | 7.5 | HOUR | 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (303 mg) was dissolved in N,N-dimethylformamide (9 mL), ethyl acrylate (0.3 mL) and potassium carbonate (538 mg) were sequentially added, and the mixture was stirred at room temperature for 7.5 hrs. Ethyl acrylate (0.2 mL) was added, and the mixture was stirred for 16 hrs. Ethyl acr... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Ester | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | null | CN(C=O)C | null | 7.5 | C=CC(=O)OCC.Clc1ncnc2cc[nH]c12>CN(C=O)C>CCOC(=O)CCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae28bb6c867541d29f3282c7a18ac86e | CS(=O)(=O)CCN.O=C(O)CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CS(=O)(=O)CCNC(=O)CCn1ccc2ncnc(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=CN2CCC(=O)NCCS(=O)(=O)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=CN2CCC(=O)O.CS(=O)(=O)CCN.Cl.CN(CCCN=C=NCC)C.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCC(=O)NCCS(=O)(=O)C.Cl.C(C)(=O)OCC>>Cl.ClC=1C=C(C=CC1OC1=CC(=CC=... | [CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][NH2:7].O[C:8](=[O: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][CH... | CS(=O)(=O)CCN.O=C(O)CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CS(=O)(=O)CCNC(=O)CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | 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]-[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] | 160 | [{"value": 160.0, "product": "Cl.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCC(=O)NCCS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]-N-[2-(methylsulfonyl)ethyl]propanamide (140 mg) was obtained by the reaction in the same manner as in Example 202 (iii) using 3-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]propanoic... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | null | null | CS(=O)(=O)CCN.O=C(O)CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC>CS(=O)(=O)CCNC(=O)CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b1eeedc5680c4a4cb7c99964c406f5af | O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21>>O=C(CCO)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(CCO)=O.ClC=1C=C(C=CC1OC1=CC(=CC=C1)OC(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CCO)=O.Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)OC(F)(F)F)Cl.O.ON1N=NC2=C1C=CC=C2.OCCC(=O)O.Cl.C(C)(=O)OCC>>Cl.ClC=1C=C(C=CC1OC1=CC(=CC=C1)OC(F)(F)F)NC=1C2=C(N=CN1)C=CN2CC... | [O:2]=[C:3]([CH2:4][CH2:5][OH: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]([NH:18][c:19]3[cH:20][cH:21][c:22]([O:23][c:24]4[cH:25][cH:26][cH:27][c:28]([O:29][C:30]([F:31])([F:32])[F:33])[cH:34]4)[c:35]([Cl:36])[cH:37]3)[c:38]12>>[O:2]=[C:3]([CH2:4][CH2:5][OH:6])[NH:7][CH2:8][CH2:9][n:10]... | O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 | O=C(CCO)NCCn1ccc2ncnc(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 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | null | null | [] | null | null | null | null | N-{2-[4-({3-Chloro-4-[3-(trifluoromethoxy)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxypropanamide was obtained by the reaction in the same manner as in Example 202 (iii) using 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethoxy)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | null | C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | null | null | O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21>C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC>O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(OC(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-727036fe3ce147629a7effcd602129c3 | COC(C)(C)OC.OCCCC(O)CO>>CC1(C)OCC(CCCO)O1 | C(C(CCCO)O)O.COC(C)(C)OC.CC1=CC=C(C=C1)S(=O)(=O)O>>CC1(OCC(O1)CCCO)C | CO[C:2](OC)([CH3:1])[CH3:3].[OH:4][CH2:5][CH:6]([CH2:7][CH2:8][CH2:9][OH:10])[OH:11]>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH:6]([CH2:7][CH2:8][CH2:9][OH:10])[O:11]1 | COC(C)(C)OC.OCCCC(O)CO | CC1(C)OCC(CCCO)O1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 64a00cd18ce80dbb6557ba4f70bb2bb92710e160014dcc8e9d84f6ab91dcc2c7 | d3cf88dd21c2b1133a535341fad8736ebfcb343cc20bb0a78301ecc79ada442a | C1COCO1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]-[OH;D1;+0:8]>>[C:4]-[C:5]1-[C:7]-[O;H0;D2;+0:8]-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:6]-1 | null | [] | null | null | 1.5 | HOUR | Pentane-1,2,5-triol (5.00 g) was dissolved in acetone (150 mL), 2,2-dimethoxypropane (10.5 mL) and 4-methylbenzenesulfonic acid (794 mg) were added, and the mixture was stirred at room temperature for 1.5 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was separated and purified by si... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Secondary alcohol | Ether.Ether | null | C1COCO1 | C1COCO1 | HO- | CC(=O)C | null | 1.5 | COC(C)(C)OC.OCCCC(O)CO>CC(=O)C>CC1(C)OCC(CCCO)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b75f8e57f0542bcb32a489ef2dbd232 | CC1(C)OCC(CCCn2ccc3ncnc(Cl)c32)O1.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>>OCC(O)CCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | ClC=1C2=C(N=CN1)C=CN2CCCC2OC(OC2)(C)C.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)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=CN2CCCC(CO)O | CC1(C)[O:1][CH2:2][CH:3]([CH2:5][CH2:6][CH2:7][n:8]2[cH:9][cH:10][c:11]3[n:12][cH:13][n:14][c:15](Cl)[c:35]23)[O:4]1.[NH2:16][c:17]1[cH:18][cH:19][c:20]([O:21][c:22]2[cH:23][cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31]2)[c:32]([Cl:33])[cH:34]1>>[OH:1][CH2:2][CH:3]([OH:4])[CH2:5][CH2:6][CH2:7][n:8]1[cH:9][cH... | CC1(C)OCC(CCCn2ccc3ncnc(Cl)c32)O1.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1 | OCC(O)CCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(C)(C)O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 778e2670924c0ed8bcf6a90c6555a3540830d12c5cbfae1b13f74f1cc5382918 | abf0b0ec18be67ff8c5cd168fe879220d788f51a7bacd61152dfeff2c16efa42 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C1(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3](-[C:4])-[O;H0;D2;+0:5]-1.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]2:[c:11]:[c:12]:[#7;a:13](-[C:14]):[c:15]:2:1.[NH2;D1;+0:16]-[c:17](:[c:18]):[c:19]>>[C:14]-[#7;a:13]1:[c:12]:[c:11]:[c:10]2:[#7;a:9]:[c:8]:[#7;a:7]:[c;H0;D3;+0:6](-[NH;D2;+0:16]-[c:17](:[c:18]):[c:19]):[c:15]:... | 61.1 | [{"value": 61.1, "product": "ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCCC(CO)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | The crude product was obtained by the reaction in the same manner as in Example 201 (iii) using 4-chloro-5-[3-(2,2-dimethyl-1,3-dioxolan-4-yl)propyl]-5H-pyrrolo[3,2-d]pyrimidine (171 mg), 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (195 mg) and isopropyl alcohol (3.5 mL). The crude product was dissolved in methanol ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Primary amine | Primary alcohol.Secondary alcohol.Secondary amine | C1COCO1.c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HCl | C(C)(C)O.CO | null | 3.5 | CC1(C)OCC(CCCn2ccc3ncnc(Cl)c32)O1.Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1>C(C)(C)O.CO>OCC(O)CCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3be30a51c2174b4691e184d20740a5a4 | O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>O=C(CCO)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(CCO)=O.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CCO)=O.Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl.O.ON1N=NC2=C1C=CC=C2.OCCC(=O)O.Cl.C(C)(=O)OCC>>Cl.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(C... | [O:2]=[C:3]([CH2:4][CH2:5][OH: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]([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>>[O:2]=[C:3]([CH2:4][CH2:5][OH:6])[NH:7][CH2:8][CH2:9][n:10]1[cH:1... | O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | null | null | [] | null | null | null | null | N-{2-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxypropanamide was obtained by the reaction in the same manner as in Example 202 (iii) using 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | null | C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | null | null | O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC>O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aac7ad5b237b4d34a24963f4d259c78f | CC(C)(C)[Si](C)(C)OCCBr.CC1(C)OCC(CO)O1>>CC1(C)OCC(COCCO[Si](C)(C)C(C)(C)C)O1 | [Cl-].[NH4+].[H-].[Na+].CC1(OCC(O1)CO)C.BrCCO[Si](C)(C)C(C)(C)C>>C(C)(C)(C)[Si](C)(C)OCCOCC1OC(OC1)(C)C | Br[CH2:9][CH2:10][O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH:6]([CH2:7][OH:8])[O:19]1>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH:6]([CH2:7][O:8][CH2:9][CH2:10][O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18])[O:19]1 | CC(C)(C)[Si](C)(C)OCCBr.CC1(C)OCC(CO)O1 | CC1(C)OCC(COCCO[Si](C)(C)C(C)(C)C)O1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | C1COCO1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[#8:4]-[C:5]-[C:6]-[OH;D1;+0:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[C:6]-[C:5]-[#8:4] | null | [] | 0 | CELSIUS | 1 | HOUR | 60% Sodium hydride (890 mg) was suspended in N,N-dimethylformamide (60 mL), and the suspension was cooled to 0° C. (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol (2.3 mL) was added dropwise and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added (2-bromoethoxy)(tert-butyl)dimethylsilane (3 mL), and t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1COCO1 | HBr | CN(C=O)C | 0 | 1 | CC(C)(C)[Si](C)(C)OCCBr.CC1(C)OCC(CO)O1>CN(C=O)C>CC1(C)OCC(COCCO[Si](C)(C)C(C)(C)C)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38e0377754744a099ec489544f1e7272 | CC1(C)OCC(COCCO[Si](C)(C)C(C)(C)C)O1.CS(=O)(=O)Cl>>CC1(C)OCC(COCCOS(C)(=O)=O)O1 | [Cl-].[NH4+].[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(C)(C)[Si](C)(C)OCCOCC1OC(OC1)(C)C.CS(=O)(=O)Cl>>CS(=O)(=O)OCCOCC1OC(OC1)(C)C | CC(C)(C)[Si](C)(C)[O:11][CH2:10][CH2:9][O:8][CH2:7][CH:6]1[CH2:5][O:4][C:2]([CH3:1])([CH3:3])[O:16]1.Cl[S:12]([CH3:13])(=[O:14])=[O:15]>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH:6]([CH2:7][O:8][CH2:9][CH2:10][O:11][S:12]([CH3:13])(=[O:14])=[O:15])[O:16]1 | CC1(C)OCC(COCCO[Si](C)(C)C(C)(C)C)O1.CS(=O)(=O)Cl | CC1(C)OCC(COCCOS(C)(=O)=O)O1 | null | null | O1CCCC1.C(C)N(CC)CC | Acylation | Formation of Sulfonic Esters on TMS protected alcohol | 9e07f5520b3bc5500a9061296fe6119923fb94fe35985540b2063263d581dc98 | acebbce8dd2300bebe4cae2d4fdddc23ab537bab21f7d9c9767166502cc48828 | C1COCO1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3].Cl-[S;H0;D4;+0:4](-[C;D1;H3:5])(=[O;D1;H0:6])=[O;D1;H0:7]>>[C:3]-[C:2]-[O;H0;D2;+0:1]-[S;H0;D4;+0:4](-[C;D1;H3:5])(=[O;D1;H0:6])=[O;D1;H0:7] | null | [] | null | null | 1 | HOUR | tert-Butyl{2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]ethoxy}dimethylsilane (1.03 g) was dissolved in tetrahydrofuran (20 mL), a 1.0 M solution (4 mL) of tetrabutylammonium fluoride in tetrahydrofuran was added, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide.TMS ether protective group | Mesylate | null | null | C1COCO1 | HCl | O1CCCC1.C(C)N(CC)CC | null | 1 | CC1(C)OCC(COCCO[Si](C)(C)C(C)(C)C)O1.CS(=O)(=O)Cl>O1CCCC1.C(C)N(CC)CC>CC1(C)OCC(COCCOS(C)(=O)=O)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66ccf0905d1247ef9bb07dee9ad0924b | Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1.OCC(O)COCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>OCC(O)COCCn1ccc2ncnc(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=CN2CCOCC(CO)O.ClC=1C2=C(N=CN1)C=CN2CCOCC2OC(OC2)(C)C.ClC=1C=C(N)C=CC1OC1=CC(=CC=C1)C(F)(F)F.Cl.C(C)(=O)OCC.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCC(CO)O>>Cl.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCOCC(CO)O | [NH2:18][c:19]1[cH:20][cH:21][c:22]([O:23][c:24]2[cH:25][cH:26][cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33]2)[c:34]([Cl:35])[cH:36]1.FC(F)(F)c1cccc(Oc2ccc(N[c:17]3[n:16][cH:15][n:14][c:13]4[cH:12][cH:11][n:10]([CH2:9][CH2:8][O:7][CH2:6][CH:4]([CH2:3][OH:2])[OH:5])[c:37]43)cc2Cl)c1>>[OH:2][CH2:3][CH:4]([OH:5])[CH2... | Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1.OCC(O)COCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | OCC(O)COCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | C(C)(C)O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | e88e7a61524392eb0cb258a4f882c1cc83f2511cff5bd223c6ff56dc8d10ae74 | ed0de786cbeaa40aae734f133871c22959d29ff35283ad441d3d1e171aa960b7 | 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:10]:3:2):c:c:c:1-O-c1:c:c:c:c(-C(-F)(-F)-F):c: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 | null | [] | null | null | null | null | 3-{2-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethoxy}propane-1,2-diol was obtained by the reaction in the same manner as in Example 237 (iv) using 4-chloro-5-{2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]ethyl}-5H-pyrrolo[3,2-d]pyrimidine (295 mg), 3-chloro-4-[3-(trifluoro... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Ether.Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1ccccc1.c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HF | C(C)(C)O.C(C)(=O)OCC | null | null | Nc1ccc(Oc2cccc(C(F)(F)F)c2)c(Cl)c1.OCC(O)COCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>C(C)(C)O.C(C)(=O)OCC>OCC(O)COCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13b49d39009f45fd8c49f218ee7219ad | CC(C)(C)OC(=O)NCC#CCCl.Clc1ncnc2cc[nH]c12>>CC(C)(C)OC(=O)NCC#CCn1ccc2ncnc(Cl)c21 | ClC=1C2=C(N=CN1)C=CN2.ClCC#CCNC(OC(C)(C)C)=O.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>>C(C)(C)(C)OC(NCC#CCN1C=CC=2N=CN=C(C21)Cl)=O | Cl[CH2:12][C:11]#[C:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[nH:13]1[cH:14][cH:15][c:16]2[n:17][cH:18][n:19][c:20]([Cl:21])[c:22]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]#[C:11][CH2:12][n:13]1[cH:14][cH:15][c:16]2[n:17][cH:18][n:19][c:20]([Cl:21])[c:22]12 | CC(C)(C)OC(=O)NCC#CCCl.Clc1ncnc2cc[nH]c12 | CC(C)(C)OC(=O)NCC#CCn1ccc2ncnc(Cl)c21 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ecfdd3ebe7f504d096c44af08936ff56b52d45d78f82ef9c3a3c3047f20010b5 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ncc2[nH]ccc2n1 | Cl-[CH2;D2;+0:1]-[C:2]#[C:3]-[C: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]:2:1>>[C:4]-[C:3]#[C:2]-[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 | 82.8 | [{"value": 82.8, "product": "C(C)(C)(C)OC(NCC#CCN1C=CC=2N=CN=C(C21)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (1.51 g), tert-butyl (4-chlorobut-2-yn-1-yl)carbamate (2.60 g), cesium carbonate (4.80 g) and N,N-dimethylformamide (15 mL) was stirred at room temperature for 2 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic l... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2[nH]ccc2n1 | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | HCl | O | null | 2 | CC(C)(C)OC(=O)NCC#CCCl.Clc1ncnc2cc[nH]c12>O>CC(C)(C)OC(=O)NCC#CCn1ccc2ncnc(Cl)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f6364c434794bd183abe416a1e7c9f7 | CC(C)(C)OC(=O)NCC#CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>Cl.NCC#CCn1ccc2ncnc(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=CN2CC#CCNC(OC(C)(C)C)=O.Cl.C(C)O>>Cl.Cl.NCC#CCN1C=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][C:5]#[C: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:2])[cH:34]3)[c:35]12>>[ClH:2].[NH2:3][CH2:4][C:5]#[C:6][CH2:7][n:8]1[cH:9][cH:10][c:11]2[n:12][cH:... | CC(C)(C)OC(=O)NCC#CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | Cl.NCC#CCn1ccc2ncnc(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]#[C:4]-[C:5].[#8:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](-[Cl;H0;D1;+0:10]):[c:11]:[c:12]>>[#8:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](-[Cl;D1;H0:13]):[c:11]:[c:12].[C:5]-[C:4]#[C:3]-[C:2]-[NH2;D1;+0:1].[ClH;D0;+0:10] | null | [] | 60 | CELSIUS | 16 | HOUR | tert-Butyl {4-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]but-2-yn-1-yl}carbamate (1.90 g) was dissolved in tetrahydrofuran (35 mL), 2N hydrochloric acid (18 mL) was added, and the mixture was stirred at 60° C. for 16 hrs. To the reaction mixture was added ethanol, and the ... | 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 | 16 | CC(C)(C)OC(=O)NCC#CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>O1CCCC1>Cl.NCC#CCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3089ba9acaa543c69e2a13e4bc2e376d | O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>O=C(CCO)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(CCO)=O.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(CCO)=O.Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl.O.ON1N=NC2=C1C=CC=C2.OCCC(=O)O.CS(=O)(=O)O>>CS(=O)(=O)O.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2... | [O:6]=[C:7]([CH2:8][CH2:9][OH:10])[NH:11][CH2:12][CH2:13][n:14]1[cH:15][cH:16][c:17]2[n:18][cH:19][n:20][c:21]([NH:22][c:23]3[cH:24][cH:25][c:26]([O:27][c:28]4[cH:29][cH:30][cH:31][c:32]([C:33]([F:34])([F:35])[F:36])[cH:37]4)[c:38]([Cl:39])[cH:40]3)[c:41]12>>[O:6]=[C:7]([CH2:8][CH2:9][OH:10])[NH:11][CH2:12][CH2:13][n:1... | O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | null | null | O1CCCC1.C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | null | null | [] | null | null | 2 | HOUR | N-{2-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxypropanamide was obtained by the reaction in the same manner as in Example 202 (iii) using 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | null | O1CCCC1.C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC | null | 2 | O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>O1CCCC1.C(C)N(CC)CC.CN(C=O)C.C(C)(=O)OCC>O=C(CCO)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43d1bb55d14042ebbcf28587c74083bd | 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.Cl | 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>>Cl.Cl.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.Cl | null | null | O1CCCC1 | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | 4812e39fa209f57a5a2564677791e5e37790c829f5742d8c7df33806c5ba4ce0 | d7ecc2e7a68b8c20d378ac6004c3fdfc3efd09bbbd9efd577186f69427135737 | 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] | null | [] | 60 | CELSIUS | 16 | HOUR | tert-Butyl {2-[4-({3-methyl-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}carbamate (2.9 g) obtained in Example 188 (i) was dissolved in tetrahydrofuran (80 mL)/2N hydrochloric acid (40 mL), and the mixture was stirred at 60° C. for 16 hrs. The reaction mixture was concentrated under... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1 | HO- | O1CCCC1 | 60 | 16 | Cc1cc(Nc2ncnc3ccn(CCNC(=O)OC(C)(C)C)c23)ccc1Oc1cccc(C(F)(F)F)c1>O1CCCC1>Cc1cc(Nc2ncnc3ccn(CCN)c23)ccc1Oc1cccc(C(F)(F)F)c1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-066edf0fe8774d78b4e156b207fb64dd | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCNC(=O)OC(C)(C)C)c34)cc2C)cn1>>Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCN)c34)cc2C)cn1.Cl.Cl | CC=1C=C(C=CC1OC=1C=NC(=CC1)C)NC=1C2=C(N=CN1)C=CN2CCNC(OC(C)(C)C)=O.Cl>>Cl.Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)C | CC(C)(C)OC(=O)[NH:22][CH2:21][CH2:20][n:19]1[cH:18][cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[cH:9][cH:8][c:7]([O:6][c:5]4[cH:4][cH:3][c:2]([CH3:1])[n:28][cH:27]4)[c:25]([CH3:26])[cH:24]3)[c:23]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][c:12]3[n:13][cH:14][n:15][c:16]4[cH:17][c... | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCNC(=O)OC(C)(C)C)c34)cc2C)cn1 | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCN)c34)cc2C)cn1.Cl.Cl | null | null | O1CCCC1 | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | 4812e39fa209f57a5a2564677791e5e37790c829f5742d8c7df33806c5ba4ce0 | d7ecc2e7a68b8c20d378ac6004c3fdfc3efd09bbbd9efd577186f69427135737 | c1cncc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | 60 | CELSIUS | 16 | HOUR | tert-Butyl {2-[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}carbamate (790 mg) was dissolved in tetrahydrofuran (24 mL)/2N hydrochloric acid (12 mL), and the mixture was stirred at 60° C. for 16 hrs. The reaction mixture was concentrated under reduced pressure, ethanol (... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccncc1.c1ccccc1.c1ncnc2cc[nH]c12 | HO- | O1CCCC1 | 60 | 16 | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCNC(=O)OC(C)(C)C)c34)cc2C)cn1>O1CCCC1>Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCN)c34)cc2C)cn1.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c1ac56260547463faad1b51a844aa013 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(OCc4ccccn4)c(Cl)c3)c21>>Cl.Cl.Cl.NCCn1ccc2ncnc(Nc3ccc(OCc4ccccn4)c(Cl)c3)c21 | C(C)(C)(C)OC(NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OCC2=NC=CC=C2)Cl)=O>>Cl.Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OCC2=NC=CC=C2)Cl | CC(C)(C)OC(=O)[NH: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][cH:26][n:27]4)[c:28]([Cl:1])[cH:30]3)[c:31]12>>[ClH:1].[ClH:2].[ClH:3].[NH2:4][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... | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(OCc4ccccn4)c(Cl)c3)c21 | Cl.Cl.Cl.NCCn1ccc2ncnc(Nc3ccc(OCc4ccccn4)c(Cl)c3)c21 | null | null | O1CCCC1.Cl | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | f9b0ddd5e086b40f0768881f9b226acdc5a9dc29f99a9283af567e925b55a3d7 | b15a28c2a3fd58b98c3a6c1b435f8c25519aeb02339cc9ac8ff8fecd35099d5c | c1ccc(COc2ccc(Nc3ncnc4cc[nH]c34)cc2)nc1 | 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] | 410.5 | [{"value": 410.5, "product": "Cl.Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OCC2=NC=CC=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 16 | HOUR | tert-Butyl[2-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethyl]carbamate (790 mg) was dissolved in tetrahydrofuran (24 mL)/2N hydrochloric acid (12 mL), and the mixture was stirred at 60° C. for 16 hrs. The reaction mixture was concentrated under reduced pressure, ethanol (30 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boc | Aromatic halide.Primary amine | c1ccccc1 | c1ccccc1 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccncc1 | HO- | O1CCCC1.Cl | 60 | 16 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(OCc4ccccn4)c(Cl)c3)c21>O1CCCC1.Cl>Cl.Cl.Cl.NCCn1ccc2ncnc(Nc3ccc(OCc4ccccn4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8988d36cb8724375af4584acc9ac0193 | Cc1cc(Nc2ncnc3ccn(CCNC(=O)[C@@H]4C[C@@H](O)CN4C(=O)OC(C)(C)C)c23)ccc1Oc1cccc(C(F)(F)F)c1.ClCCl>>Cc1cc(Nc2ncnc3ccn(CCNC(=O)[C@@H]4C[C@@H](O)CN4)c23)ccc1Oc1cccc(C(F)(F)F)c1.Cl.Cl | O[C@@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(=O)NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)C.ClCCl.FC(C(=O)O)(F)F>>Cl.Cl.O[C@@H]1C[C@H](NC1)C(=O)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)[N:24]1[C@H:19]([C:17]([NH:16][CH2:15][CH2:14][n:13]2[cH:12][cH:11][c:10]3[n:9][cH:8][n:7][c:6]([NH:5][c:4]4[cH:3][c:2]([CH3:1])[c:28]([O:29][c:30]5[cH:31][cH:32][cH:33][c:34]([C:35]([F:36])([F:37])[F:38])[cH:39]5)[cH:27][cH:26]4)[c:25]32)=[O:18])[CH2:20][C@@H:21]([OH:22])[CH2:23]1.C([Cl:40])[Cl:41]>>[CH3... | Cc1cc(Nc2ncnc3ccn(CCNC(=O)[C@@H]4C[C@@H](O)CN4C(=O)OC(C)(C)C)c23)ccc1Oc1cccc(C(F)(F)F)c1.ClCCl | Cc1cc(Nc2ncnc3ccn(CCNC(=O)[C@@H]4C[C@@H](O)CN4)c23)ccc1Oc1cccc(C(F)(F)F)c1.Cl.Cl | null | null | null | Miscellaneous | OtherReaction | 3d13376f22099a603cf8d03ba2bae39027a371e34833ba8f6048c2d87eee4b71 | 016f034d4f383e2d40e897f441602a7d95bad94b528953d03d8a2ec434dca97e | O=C(NCCn1ccc2ncnc(Nc3ccc(Oc4ccccc4)cc3)c21)[C@@H]1CCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9].[Cl;H0;D1;+0:10]-C-[Cl;H0;D1;+0:11]>>[C:9]-[#7:8]-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1.[ClH;D0;+0:10].[ClH;D0;+0:11] | null | [] | null | null | 2 | HOUR | tert-Butyl (2S,4R)-4-hydroxy-2-[({2-[4-({3-methyl-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}amino)carbonyl]pyrrolidine-1-carboxylate (230 mg) was dissolved in dichloromethane (2.39 mL), trifluoroacetic acid (1.79 mL) was added, and the mixture was stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | c1ccccc1.c1ncnc2cc[nH]c12.C1CCNC1.c1ccccc1 | HO- | null | null | 2 | Cc1cc(Nc2ncnc3ccn(CCNC(=O)[C@@H]4C[C@@H](O)CN4C(=O)OC(C)(C)C)c23)ccc1Oc1cccc(C(F)(F)F)c1.ClCCl>>Cc1cc(Nc2ncnc3ccn(CCNC(=O)[C@@H]4C[C@@H](O)CN4)c23)ccc1Oc1cccc(C(F)(F)F)c1.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1206b0d56e3440eb8baf39b4de1476e3 | Cc1cc(Nc2ncnc3ccn(CCNC(=O)CS(C)(=O)=O)c23)ccc1Oc1cccc(C(F)(F)F)c1>>Cc1cc(Nc2ncnc3ccn(CCNC(=O)CS(C)(=O)=O)c23)ccc1Oc1cccc(C(F)(F)F)c1 | CS(=O)(=O)CC(=O)NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)C.CS(=O)(=O)O>>CS(=O)(=O)O.CS(=O)(=O)CC(=O)NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)C | [CH3:6][c:7]1[cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][n:14][c:15]3[cH:16][cH:17][n:18]([CH2:19][CH2:20][NH:21][C:22](=[O:23])[CH2:24][S:25]([CH3:26])(=[O:27])=[O:28])[c:29]23)[cH:30][cH:31][c:32]1[O:33][c:34]1[cH:35][cH:36][cH:37][c:38]([C:39]([F:40])([F:41])[F:42])[cH:43]1>>[CH3:6][c:7]1[cH:8][c:9]([NH:10][c:11]2[n:12]... | Cc1cc(Nc2ncnc3ccn(CCNC(=O)CS(C)(=O)=O)c23)ccc1Oc1cccc(C(F)(F)F)c1 | Cc1cc(Nc2ncnc3ccn(CCNC(=O)CS(C)(=O)=O)c23)ccc1Oc1cccc(C(F)(F)F)c1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | null | null | [] | null | null | 10 | MINUTE | 2-(Methylsulfonyl)-N-{2-[4-({3-methyl-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}acetamide (680 mg) was dissolved in ethyl acetate (3.4 mL), methanesulfonic acid (0.0887 mL) was added at 50° C., and the mixture was stirred for 10 min. and further stirred at room temperature for 2 ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1 | null | C(C)(=O)OCC | null | 0.166667 | Cc1cc(Nc2ncnc3ccn(CCNC(=O)CS(C)(=O)=O)c23)ccc1Oc1cccc(C(F)(F)F)c1>C(C)(=O)OCC>Cc1cc(Nc2ncnc3ccn(CCNC(=O)CS(C)(=O)=O)c23)ccc1Oc1cccc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-739d42940f924f468639aa15c41653b5 | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCNC(=O)OC(C)(C)C)c34)cc2Cl)cn1>>Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCN)c34)cc2Cl)cn1.Cl.Cl.Cl | ClC=1C=C(C=CC1OC=1C=NC(=CC1)C)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)OC=2C=NC(=CC2)C)Cl | CC(C)(C)OC(=O)[NH:22][CH2:21][CH2:20][n:19]1[cH:18][cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[cH:9][cH:8][c:7]([O:6][c:5]4[cH:4][cH:3][c:2]([CH3:1])[n:28][cH:27]4)[c:25]([Cl:26])[cH:24]3)[c:23]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][c:12]3[n:13][cH:14][n:15][c:16]4[cH:17][cH... | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCNC(=O)OC(C)(C)C)c34)cc2Cl)cn1 | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCN)c34)cc2Cl)cn1.Cl.Cl.Cl | null | null | O1CCCC1.Cl | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | 4812e39fa209f57a5a2564677791e5e37790c829f5742d8c7df33806c5ba4ce0 | d7ecc2e7a68b8c20d378ac6004c3fdfc3efd09bbbd9efd577186f69427135737 | c1cncc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 394.5 | [{"value": 394.5, "product": "Cl.Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC(=CC2)C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 16 | HOUR | tert-Butyl {2-[4-({3-chloro-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}carbamate (643 mg) was dissolved in tetrahydrofuran (19.5 mL)/2N hydrochloric acid (9.75 mL), and the mixture was stirred at 60° C. for 16 hrs. The reaction mixture was concentrated under reduced pressure, ethan... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccncc1.c1ccccc1.c1ncnc2cc[nH]c12 | HO- | O1CCCC1.Cl | 60 | 16 | Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCNC(=O)OC(C)(C)C)c34)cc2Cl)cn1>O1CCCC1.Cl>Cc1ccc(Oc2ccc(Nc3ncnc4ccn(CCN)c34)cc2Cl)cn1.Cl.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b25460c3526e400fbf67d72aa76ce5f2 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cncc(Cl)c4)c(Cl)c3)c21>>Cl.Cl.Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cncc(Cl)c4)c(Cl)c3)c21 | ClC=1C=C(C=CC1OC=1C=NC=C(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)OC=2C=NC=C(C2)Cl)Cl | CC(C)(C)OC(=O)[NH: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][c:21]4[cH:22][n:23][cH:24][c:25]([Cl:26])[cH:27]4)[c:28]([Cl:1])[cH:30]3)[c:31]12>>[ClH:1].[ClH:2].[ClH:3].[NH2:4][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... | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cncc(Cl)c4)c(Cl)c3)c21 | Cl.Cl.Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cncc(Cl)c4)c(Cl)c3)c21 | null | null | O1CCCC1.Cl | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | f9b0ddd5e086b40f0768881f9b226acdc5a9dc29f99a9283af567e925b55a3d7 | b15a28c2a3fd58b98c3a6c1b435f8c25519aeb02339cc9ac8ff8fecd35099d5c | c1cncc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)c1 | 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] | 372.2 | [{"value": 372.2, "product": "Cl.Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC=2C=NC=C(C2)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 16 | HOUR | tert-Butyl {2-[4-({3-chloro-4-[(5-chloropyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}carbamate (700 mg) was dissolved in tetrahydrofuran (19.5 mL)/2N hydrochloric acid (9.75 mL), and the mixture was stirred at 60° C. for 16 hrs. The reaction mixture was concentrated under reduced pressure, ethan... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boc | Aromatic halide.Primary amine | c1ccccc1 | c1ccccc1 | c1ncnc2cc[nH]c12.c1ccccc1.c1ccncc1 | HO- | O1CCCC1.Cl | 60 | 16 | CC(C)(C)OC(=O)NCCn1ccc2ncnc(Nc3ccc(Oc4cncc(Cl)c4)c(Cl)c3)c21>O1CCCC1.Cl>Cl.Cl.Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cncc(Cl)c4)c(Cl)c3)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a447af30e9f43128ca371e783d545cd | CC(C)(C)OC(=O)N1CCC(Oc2ccc(N)cc2Cl)CC1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1>>CC(C)(C)OC(=O)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)CC1 | C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)Cl.NC1=CC(=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C=C1)Cl>>C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(OC1CCN(CC1)C(=O)OC(C)(C)C)C=C2)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][cH:15][c:16]([NH2:17])[cH:41][c:42]2[Cl:43])[CH2:44][CH2:45]1.Cl[c:18]1[n:19][cH:20][n:21][c:22]2[cH:23][cH:24][n:25]([CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][C:32](=[O:33])[c:34]3[cH:35][cH:36][cH:37][cH:38][cH:39]3)[... | CC(C)(C)OC(=O)N1CCC(Oc2ccc(N)cc2Cl)CC1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1 | CC(C)(C)OC(=O)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)CC1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OC4CCNCC4)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 | 73.8 | [{"value": 73.8, "product": "C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(OC1CCN(CC1)C(=O)OC(C)(C)C)C=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 8 | HOUR | A mixture of 2-[2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy]ethyl benzoate (3.46 g), tert-butyl 4-(4-amino-2-chlorophenoxy)piperidine-1-carboxylate (3.27 g) and isopropyl alcohol (50 mL) was stirred at 80° C. overnight. The reaction mixture was concentrated under reduced pressure, water and saturated aqueous sod... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | C1CC[NH]CC1.c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1 | HCl | C(C)(C)O | 80 | 8 | CC(C)(C)OC(=O)N1CCC(Oc2ccc(N)cc2Cl)CC1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1>C(C)(C)O>CC(C)(C)OC(=O)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3559578cd4894683bf480130268e4df3 | CC(C)(C)OC(=O)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)CC1 | C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(OC1CCN(CC1)C(=O)OC(C)(C)C)C=C2)Cl.O>>ClC1=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C=CC(=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO | O=C(c1ccccc1)[O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][n:25]1[cH:24][cH:23][c:22]2[n:21][cH:20][n:19][c:18]([NH:17][c:16]3[cH:15][cH:14][c:13]([O:12][CH:11]4[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH2:36]4)[c:34]([Cl:35])[cH:33]3)[c:32]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:... | CC(C)(C)OC(=O)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)CC1 | null | null | O1CCCC1.CO.[OH-].[Na+] | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 8df1b5c4ec88eb8f4e334a9ade2ac7fc0b3f460ea1450816d1758f28eee39662 | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1nc(Nc2ccc(OC3CCNCC3)cc2)c2[nH]ccc2n1 | 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] | 93.6 | [{"value": 93.6, "product": "ClC1=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C=CC(=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | tert-Butyl 4-{4-[(5-{2-[2-(benzoyloxy)ethoxy]ethyl}-5H-pyrrolo[3,2-d]pyrimidin-4-yl)amino]-2-chlorophenoxy}piperidine-1-carboxylate (636 mg) was dissolved in a mixed solvent of methanol (10 mL) and tetrahydrofuran (10 mL), 1N aqueous sodium hydroxide solution (2 mL) was added, and the mixture was stirred overnight at r... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | c1ccccc1 | null | C1CC[NH]CC1.c1ccccc1.c1ncnc2cc[nH]c12 | HO- | O1CCCC1.CO.[OH-].[Na+] | null | 8 | CC(C)(C)OC(=O)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)CC1>O1CCCC1.CO.[OH-].[Na+]>CC(C)(C)OC(=O)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-61723fdf027b4fffbd014f52b48ec0c5 | CC(C)(C)OC(=O)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)CC1>>Cl.O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OC4CCNCC4)c(Cl)c3)c21)c1ccccc1 | Cl.C(C)(=O)OCC.C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(OC1CCN(CC1)C(=O)OC(C)(C)C)C=C2)Cl>>Cl.Cl.C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2CCNCC2)Cl | CC(C)(C)OC(=O)[N:28]1[CH2:27][CH2:26][CH:25]([O:24][c:23]2[cH:22][cH:21][c:20]([NH:19][c:18]3[n:17][cH:16][n:15][c:14]4[cH:13][cH:12][n:11]([CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][C:4](=[O:3])[c:35]5[cH:36][cH:37][cH:38][cH:39][cH:40]5)[c:34]43)[cH:33][c:31]2[Cl:1])[CH2:30][CH2:29]1>>[ClH:1].[O:3]=[C:4]([O:5][CH2:6][CH... | CC(C)(C)OC(=O)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)CC1 | Cl.O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OC4CCNCC4)c(Cl)c3)c21)c1ccccc1 | null | null | C(C)O | Miscellaneous | Boc amine deprotection | ce4c3ea9d0c2faff3b9f7452f75b24d2d30bf40e954020ffa8aa94c1924df770 | 8eaac4d88ccfd676cb152ac8731ddb039e8a75c2631f9792b0a36d78d07a9740 | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OC4CCNCC4)cc3)c21)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[#8:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](-[Cl;H0;D1;+0:10]):[c:11]:[c:12]>>[#8:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](-[Cl;D1;H0:13]):[c:11]:[c:12].[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5].[ClH;D0;+0:10] | null | [] | null | null | 5 | HOUR | 4N Hydrochloric acid/ethyl acetate solution (20 mL) and ethanol (10 mL) were added to tert-butyl 4-{4-[(5-{2-[2-(benzoyloxy)ethoxy]ethyl}-5H-pyrrolo[3,2-d]pyrimidin-4-yl)amino]-2-chlorophenoxy}piperidine-1-carboxylate (3.82 g), and the mixture was stirred at room temperature for 5 hrs. The reaction mixture was concentr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boc | Aromatic halide.Secondary amine | C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CCNCC1 | c1ncnc2cc[nH]c12.c1ccccc1.C1CCNCC1.c1ccccc1 | HO- | C(C)O | null | 5 | CC(C)(C)OC(=O)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)CC1>C(C)O>Cl.O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OC4CCNCC4)c(Cl)c3)c21)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b5f1f56301ff4b608fed21fa38c80fa3 | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OC4CCNCC4)c(Cl)c3)c21)c1ccccc1.O=C=Nc1c(F)cccc1F>>O=C(Nc1c(F)cccc1F)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)CC1 | FC1=C(C(=CC=C1)F)N=C=O.Cl.Cl.C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2CCNCC2)Cl.C([O-])([O-])=O.[Na+].[Na+].C(C)(=O)OCC>>Cl.ClC1=C(OC2CCN(CC2)C(=O)NC2=C(C=CC=C2F)F)C=CC(=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO | O=C(c1ccccc1)[O:36][CH2:35][CH2:34][O:33][CH2:32][CH2:31][n:30]1[cH:29][cH:28][c:27]2[n:26][cH:25][n:24][c:23]([NH:22][c:21]3[cH:20][cH:19][c:18]([O:17][CH:16]4[CH2:15][CH2:14][NH:13][CH2:42][CH2:41]4)[c:39]([Cl:40])[cH:38]3)[c:37]21.[O:2]=[C:3]=[N:4][c:5]1[c:6]([F:7])[cH:8][cH:9][cH:10][c:11]1[F:12]>>[O:2]=[C:3]([NH:4... | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OC4CCNCC4)c(Cl)c3)c21)c1ccccc1.O=C=Nc1c(F)cccc1F | O=C(Nc1c(F)cccc1F)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)CC1 | null | null | O1CCCC1.O | Acylation | OtherReaction | 3d5daa558c514eafe4a8e588e22c05699c195e8e75bc26b521cf6a1e2dce1526 | 06668a26d5e7eeaa79479805e8a93d257d5e64cf3a8d52ffd96b865a7e33864c | O=C(Nc1ccccc1)N1CCC(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)CC1 | O=C(-[O;H0;D2;+0:1]-[C:2]-[C:3])-c1:c:c:c:c:c:1.[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8].[O;D1;H0:9]=[C;H0;D2;+0:10]=[N;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C;H0;D3;+0:10](=[O;D1;H0:9])-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C:7]-[C:8].[C:3]-[C:2]-[OH;D1;+0:1] | 129.4 | [{"value": 129.4, "product": "Cl.ClC1=C(OC2CCN(CC2)C(=O)NC2=C(C=CC=C2F)F)C=CC(=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of 2-[2-(4-{[3-chloro-4-(piperidin-4-yloxy)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy]ethyl benzoate dihydrochloride (305 mg), 10% aqueous sodium carbonate solution (10 mL), ethyl acetate (15 mL) and tetrahydrofuran (5 mL) was added 2,6-difluorophenyl isocyanate (93 mg) with vigorous stirring. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Isocyanate.Secondary amine | Urea.Primary alcohol | c1ccccc1.C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ncnc2cc[nH]c12 | HO- | O1CCCC1.O | null | 2 | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OC4CCNCC4)c(Cl)c3)c21)c1ccccc1.O=C=Nc1c(F)cccc1F>O1CCCC1.O>O=C(Nc1c(F)cccc1F)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c8d45ef7341e4a259527df19d4d59b92 | NC1CCCC1.O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OC4CCNCC4)c(Cl)c3)c21)c1ccccc1.O=C(n1ccnc1)n1ccnc1>>O=C(NC1CCCC1)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)CC1 | C(=O)(N1C=NC=C1)N1C=NC=C1.C1(CCCC1)N.Cl.Cl.C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2CCNCC2)Cl.C(C)N(CC)CC>>Cl.ClC1=C(OC2CCN(CC2)C(=O)NC2CCCC2)C=CC(=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO | [NH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1.O=C(c1ccccc1)[O:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][n:27]1[cH:26][cH:25][c:24]2[n:23][cH:22][n:21][c:20]([NH:19][c:18]3[cH:17][cH:16][c:15]([O:14][CH:13]4[CH2:12][CH2:11][NH:10][CH2:39][CH2:38]4)[c:36]([Cl:37])[cH:35]3)[c:34]21.c1cn([C:3](n2ccnc2)=[O:2])cn1>>[O:2]=[C:3]... | NC1CCCC1.O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OC4CCNCC4)c(Cl)c3)c21)c1ccccc1.O=C(n1ccnc1)n1ccnc1 | O=C(NC1CCCC1)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)CC1 | null | null | O1CCCC1.O | Acylation | OtherReaction | 22d4a029fb0269f180201dea5604d2f55ee37dab9d1efc34f915507d4c3359e6 | 14aff967099df1655de24622d6738511aed25e5de6dfcd9146c67d3e73427243 | O=C(NC1CCCC1)N1CCC(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)CC1 | O=C(-[O;H0;D2;+0:1]-[C:2]-[C:3])-c1:c:c:c:c:c:1.[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12].[O;D1;H0:13]=[C;H0;D3;+0:14](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C;H0;D3;+0:14](=[O;D1;H0:13])-[NH;D2;+0:11]-[C:10](-[C:9])-[C:12])-[C:7]-[C:8].[C:3]-[C:2]-[OH;D1;+0:1] | 129.5 | [{"value": 129.5, "product": "Cl.ClC1=C(OC2CCN(CC2)C(=O)NC2CCCC2)C=CC(=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 1,1′-carbonylbis(1H-imidazole) (162 mg) in tetrahydrofuran (5 mL) was added a solution of cyclopentylamine (85 mg) in tetrahydrofuran (1 mL), and the mixture was stirred at room temperature for 1 hr. A solution of 2-[2-(4-{[3-chloro-4-(piperidin-4-yloxy)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-5-yl)eth... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Secondary amine | Urea.Primary alcohol | c1ccccc1.C1CCNCC1.c1c[nH]cn1.c1c[nH]cn1 | C1CC[NH]CC1 | C1CCCC1.C1CC[NH]CC1.c1ccccc1.c1ncnc2cc[nH]c12 | HO- | O1CCCC1.O | null | 1 | NC1CCCC1.O=C(OCCOCCn1ccc2ncnc(Nc3ccc(OC4CCNCC4)c(Cl)c3)c21)c1ccccc1.O=C(n1ccnc1)n1ccnc1>O1CCCC1.O>O=C(NC1CCCC1)N1CCC(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1d8295f4118c443f845dfe6d506868df | CC(C)(C)OC(=O)c1ccc(Oc2ccc(N)cc2Cl)cc1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1>>CC(C)(C)OC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1 | C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)Cl.NC1=CC(=C(OC2=CC=C(C(=O)OC(C)(C)C)C=C2)C=C1)Cl>>C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(OC1=CC=C(C(=O)OC(C)(C)C)C=C1)C=C2)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][c:16]([NH2:17])[cH:41][c:42]2[Cl:43])[cH:44][cH:45]1.Cl[c:18]1[n:19][cH:20][n:21][c:22]2[cH:23][cH:24][n:25]([CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][C:32](=[O:33])[c:34]3[cH:35][cH:36][cH:37][cH:38][cH:39]3)[c:40]... | CC(C)(C)OC(=O)c1ccc(Oc2ccc(N)cc2Cl)cc1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1 | CC(C)(C)OC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | b3e82b6ead9cdf4e2f8cbbcf91109747f4dd1119eb8fb5a3a7a9710387d7d6e5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(Oc4ccccc4)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 | 58 | [{"value": 58.0, "product": "C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(OC1=CC=C(C(=O)OC(C)(C)C)C=C1)C=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 8 | HOUR | A mixture of 2-[2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy]ethyl benzoate (1.46 g), tert-butyl 4-(4-amino-2-chlorophenoxy)benzoate (1.35 g) and isopropyl alcohol (30 mL) was stirred at 80° C. overnight. The reaction mixture was concentrated under reduced pressure, water and saturated aqueous sodium hydrogen car... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncnc2cc[nH]c12 | c1ncnc2cc[nH]c12 | c1ccccc1.c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1 | HCl | C(C)(C)O | 80 | 8 | CC(C)(C)OC(=O)c1ccc(Oc2ccc(N)cc2Cl)cc1.O=C(OCCOCCn1ccc2ncnc(Cl)c21)c1ccccc1>C(C)(C)O>CC(C)(C)OC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb3ce3baa25c49f88b01937ad41ccc0d | CC(C)(C)OC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1>>CC(C)(C)OC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)cc1.Cl | C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(OC1=CC=C(C(=O)OC(C)(C)C)C=C1)C=C2)Cl.O>>Cl.ClC1=C(OC2=CC=C(C(=O)OC(C)(C)C)C=C2)C=CC(=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO | O=C(c1ccccc1)[O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][n:25]1[cH:24][cH:23][c:22]2[n:21][cH:20][n:19][c:18]([NH:17][c:16]3[cH:15][cH:14][c:13]([O:12][c:11]4[cH:10][cH:9][c:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:37][cH:36]4)[c:34]([Cl:35])[cH:33]3)[c:32]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[... | CC(C)(C)OC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1 | CC(C)(C)OC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)cc1.Cl | null | null | O1CCCC1.CO.[OH-].[Na+] | Miscellaneous | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 75c7457e3a9fb6f1ba09eb81042cf77dcdbcc742bd16c83aaeebe9a9679aff92 | 6c68e56451f63eb914da47d835c80c50f16b8e098a52b924c7914bb1a69fa96c | c1ccc(Oc2ccc(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] | 193.3 | [{"value": 193.3, "product": "Cl.ClC1=C(OC2=CC=C(C(=O)OC(C)(C)C)C=C2)C=CC(=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | tert-Butyl 4-{4-[(5-{2-[2-(benzoyloxy)ethoxy]ethyl}-5H-pyrrolo[3,2-d]pyrimidin-4-yl)amino]-2-chlorophenoxy}benzoate (189 mg) was dissolved in a mixed solvent of methanol (5 mL) and tetrahydrofuran (1 mL), 1N aqueous sodium hydroxide solution (0.6 mL) was added, and the mixture was stirred overnight at room temperature.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ncnc2cc[nH]c12 | HO- | O1CCCC1.CO.[OH-].[Na+] | null | 8 | CC(C)(C)OC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1>O1CCCC1.CO.[OH-].[Na+]>CC(C)(C)OC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)cc1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea89cb9c33614f4182b2a959ee003cb3 | CC(C)(C)OC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1>>Cl.O=C(O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1 | C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(OC1=CC=C(C(=O)OC(C)(C)C)C=C1)C=C2)Cl>>Cl.C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(OC1=CC=C(C(=O)O)C=C1)C=C2)Cl | CC(C)(C)[O:4][C:3](=[O:2])[c:5]1[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][O:28][C:29](=[O:30])[c:31]5[cH:32][cH:33][cH:34][cH:35][cH:36]5)[c:37]34)[cH:38][c:39]2[Cl:1])[cH:41][cH:42]1>>[ClH:1].[O:2]=[C:3]([OH:4]... | CC(C)(C)OC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1 | Cl.O=C(O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1 | null | null | FC(C(=O)O)(F)F | Functional Group Interconversion | Deprotection of carboxylic acid | 2925f84c790135189a05fa87f9d873359f8ae83f30057d47d934c52331b0a572 | 882ec6822f5a850b1be02ee0d833b619e124b3402656234509adb466b745d330 | O=C(OCCOCCn1ccc2ncnc(Nc3ccc(Oc4ccccc4)cc3)c21)c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[Cl;H0;D1;+0:9]):[c:10]:[c:11]>>[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[Cl;D1;H0:12]):[c:10]:[c:11].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[ClH;D0;+0:9] | 190.1 | [{"value": 190.1, "product": "Cl.C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(OC1=CC=C(C(=O)O)C=C1)C=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Trifluoroacetic acid (10 mL) was added to tert-butyl 4-{4-[(5-{2-[2-(benzoyloxy)ethoxy]ethyl}-5H-pyrrolo[3,2-d]pyrimidin-4-yl)amino]-2-chlorophenoxy}benzoate (1.26 g), and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was concentrated under reduced pressure, 4N hydrochloric acid/ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boc | Aromatic halide.Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ncnc2cc[nH]c12.c1ccccc1 | Other | FC(C(=O)O)(F)F | null | 3 | CC(C)(C)OC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1>FC(C(=O)O)(F)F>Cl.O=C(O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e05cd2b1739249729b201ad1248b5921 | CC(C)(C)N.O=C(O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1>>CC(C)(C)NC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)cc1 | Cl.C(C1=CC=CC=C1)(=O)OCCOCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(OC1=CC=C(C(=O)O)C=C1)C=C2)Cl.CC(C)(C)N.Cl.C(C)N=C=NCCCN(C)C.O.ON1N=NC2=C1C=CC=C2>>Cl.C(C)(C)(C)NC(C1=CC=C(C=C1)OC1=C(C=C(C=C1)NC=1C2=C(N=CN1)C=CN2CCOCCO)Cl)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[NH2:5].O=C(c1ccccc1)[O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][n:25]1[cH:24][cH:23][c:22]2[n:21][cH:20][n:19][c:18]([NH:17][c:16]3[cH:15][cH:14][c:13]([O:12][c:11]4[cH:10][cH:9][c:8]([C:6](O)=[O:7])[cH:37][cH:36]4)[c:34]([Cl:35])[cH:33]3)[c:32]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:... | CC(C)(C)N.O=C(O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1 | CC(C)(C)NC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)cc1 | null | null | O.C(C)N(CC)CC.CN(C=O)C | Acylation | OtherReaction | 841820a51f305a54d171f5504c9b8e43f1508e4bf73cd8b690ba0db9886e7c72 | 5f68606e1652dcb7d724fc9313be32cd73fe12aa10c1a7ff593e99a300f09c8e | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=C(-[O;H0;D2;+0:6]-[C:7]-[C:8])-c1:c:c:c:c:c:1.[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH2;D1;+0:13]>>[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:8]-[C:7]-[OH;D1;+0:6] | null | [] | null | null | 8 | HOUR | A mixture of 4-{4-[(5-{2-[2-(benzoyloxy)ethoxy]ethyl}-5H-pyrrolo[3,2-d]pyrimidin-4-yl)amino]-2-chlorophenoxy}benzoic acid hydrochloride (183 mg), 2-methylpropan-2-amine (0.038 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (69 mg), 1-hydroxybenzotriazole monohydrate (55 mg), triethylamine (0.050 mL) a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Primary amine | Secondary amide.Primary alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ncnc2cc[nH]c12 | HO- | O.C(C)N(CC)CC.CN(C=O)C | null | 8 | CC(C)(C)N.O=C(O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCOC(=O)c5ccccc5)c34)cc2Cl)cc1>O.C(C)N(CC)CC.CN(C=O)C>CC(C)(C)NC(=O)c1ccc(Oc2ccc(Nc3ncnc4ccn(CCOCCO)c34)cc2Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69a6a307d91545ee921a24863af1aeca | CN(C(=O)OC(C)(C)C)C(=NC(=O)OC(C)(C)C)n1cccn1.Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>>CNC(=N)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.Cl | O.CN(C(=NC(=O)OC(C)(C)C)N1N=CC=C1)C(=O)OC(C)(C)C.C(C)N(C(C)C)C(C)C.Cl.Cl.NCCN1C=CC=2N=CN=C(C21)NC2=CC(=C(C=C2)OC2=CC(=CC=C2)C(F)(F)F)Cl>>Cl.Cl.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(=N)NC | CC(C)(C)OC(=O)[N:2]([CH3:1])[C:3](n1cccn1)=[N:4]C(=O)OC(C)(C)C.[ClH:37].[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>>[CH3:1][NH:2][C:3](=[NH:4])... | CN(C(=O)OC(C)(C)C)C(=NC(=O)OC(C)(C)C)n1cccn1.Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21 | CNC(=N)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.Cl | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 74ac281d7376101e04892b698126e6c95ded993b43965c546e5a0d6545da3e9b | a03ac3c151f67cf6329b1139a3d31f02d5af7d1dceec1cac28a151c281788780 | c1ccc(Oc2ccc(Nc3ncnc4cc[nH]c34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D2;+0:1]=[C;H0;D3;+0:2](-[N;H0;D3;+0:3](-[C;D1;H3:4])-C(=O)-O-C(-C)(-C)-C)-n1:c:c:c:n:1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:2](=[NH;D1;+0:1])-[NH;D2;+0:3]-[C;D1;H3:4] | 88.5 | [{"value": 88.5, "product": "Cl.Cl.ClC=1C=C(C=CC1OC1=CC(=CC=C1)C(F)(F)F)NC=1C2=C(N=CN1)C=CN2CCNC(=N)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | To a solution of N-methyl-N,N′-bis(tert-butoxy carbonyl)-1H-pyrazole-1-carboxamidine (138 mg) and ethyldiisopropylamine (0.16 mL) in acetonitrile (4 mL) was added 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (200 mg), and the mixture was stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Primary amine.Boc.Boc | Secondary amine.Secondary amine | c1cn[nH]c1 | null | c1ncnc2cc[nH]c12.c1ccccc1.c1ccccc1 | HO- | C(C)#N | null | 96 | CN(C(=O)OC(C)(C)C)C(=NC(=O)OC(C)(C)C)n1cccn1.Cl.NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21>C(C)#N>CNC(=N)NCCn1ccc2ncnc(Nc3ccc(Oc4cccc(C(F)(F)F)c4)c(Cl)c3)c21.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d36e84f0fd644ef7b9900b0fd0ff2d69 | O=[N+]([O-])c1ccc(F)c(Cl)c1.Oc1ccc(CCCn2ccnc2)cc1>>O=[N+]([O-])c1ccc(Oc2ccc(CCCn3ccnc3)cc2)c(Cl)c1 | O.N1(C=NC=C1)CCCC1=CC=C(C=C1)O.ClC=1C=C(C=CC1F)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+]>>ClC=1C=C(C=CC1OC1=CC=C(C=C1)CCCN1C=NC=C1)[N+](=O)[O-] | F[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:25][c:23]1[Cl:24].[OH:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][CH2:15][n:16]2[cH:17][cH:18][n:19][cH:20]2)[cH:21][cH:22]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]([CH2:13][CH2:14][CH2:15][n:16]3[cH:17][cH:18][n:19][cH:20]3)[cH:21... | O=[N+]([O-])c1ccc(F)c(Cl)c1.Oc1ccc(CCCn2ccnc2)cc1 | O=[N+]([O-])c1ccc(Oc2ccc(CCCn3ccnc3)cc2)c(Cl)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccc(CCCn3ccnc3)cc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:2]:[c:3] | 93.4 | [{"value": 93.4, "product": "ClC=1C=C(C=CC1OC1=CC=C(C=C1)CCCN1C=NC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 4-[3-(1H-imidazol-1-yl)propyl]phenol (405 mg) and 3-chloro-4-fluoronitrobenzene (370 mg) in N,N-dimethylformamide (4 mL) was added potassium carbonate (415 mg), and the mixture was stirred at room temperature for 16 hrs. Under ice-cooling, water was added and the mixture was extracted with ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1c[nH]cn1 | HF | CN(C=O)C | null | 16 | O=[N+]([O-])c1ccc(F)c(Cl)c1.Oc1ccc(CCCn2ccnc2)cc1>CN(C=O)C>O=[N+]([O-])c1ccc(Oc2ccc(CCCn3ccnc3)cc2)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f3ea9e203b14268bbef232e96c7413e | O=[N+]([O-])c1ccc(Oc2ccc(CCCn3ccnc3)cc2)c(Cl)c1>>Nc1ccc(Oc2ccc(CCCn3ccnc3)cc2)c(Cl)c1 | ClC=1C=C(C=CC1OC1=CC=C(C=C1)CCCN1C=NC=C1)[N+](=O)[O-]>>ClC=1C=C(N)C=CC1OC1=CC=C(C=C1)CCCN1C=NC=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([CH2:11][CH2:12][CH2:13][n:14]3[cH:15][cH:16][n:17][cH:18]3)[cH:19][cH:20]2)[c:21]([Cl:22])[cH:23]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][c:10]([CH2:11][CH2:12][CH2:13][n:14]3[cH:15][cH:16][n:17][cH:18]3)[cH:19][cH:20]2)[c:21]([Cl:22]... | O=[N+]([O-])c1ccc(Oc2ccc(CCCn3ccnc3)cc2)c(Cl)c1 | Nc1ccc(Oc2ccc(CCCn3ccnc3)cc2)c(Cl)c1 | null | [Pt] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccc(CCCn3ccnc3)cc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 45.2 | [{"value": 45.2, "product": "ClC=1C=C(N)C=CC1OC1=CC=C(C=C1)CCCN1C=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 3-chloro-4-{4-[3-(1H-imidazol-1-yl)propyl]phenoxy}nitrobenzene (669 mg) in methanol (7 mL) was added 5% Pt/C (140 mg), and the mixture was stirred under hydrogen atmosphere at room temperature for 16 hrs. 5% Pt/C was filtered off and the filtrate was concentrated. The residue was purified by basic sili... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1.c1c[nH]cn1 | Other | [Pt].CO | null | 16 | O=[N+]([O-])c1ccc(Oc2ccc(CCCn3ccnc3)cc2)c(Cl)c1>[Pt].CO>Nc1ccc(Oc2ccc(CCCn3ccnc3)cc2)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89b849bfcf45431dbc41fad8bbb3c08c | CC(C)c1ccc(C=O)cc1.[OH-]>>CC(C)c1ccc(C(O)C(=O)O)cc1 | [Cl-].[Li+].[OH-].[K+].Cl.C(Br)(Br)Br.C(C)(C)C1=CC=C(C=O)C=C1.O1CCOCC1>>OC(C(=O)O)C1=CC=C(C=C1)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]=[O:9])[cH:13][cH:14]1.[OH-:12]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]([OH:9])[C:10](=[O:11])[OH:12])[cH:13][cH:14]1 | CC(C)c1ccc(C=O)cc1.[OH-] | CC(C)c1ccc(C(O)C(=O)O)cc1 | null | null | null | Acylation | OtherReaction | e4754e3793ba0362af7cd262e2f320471fced6da69cfa59aaf69349f987b0106 | 7b79ddb9582ae558ef0424125dcd16c236a764b78e4d8d3057436676b03c02cd | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5].[OH-;D0:6]>>[O;D1;H0:7]=[C:8](-[OH;D1;+0:6])-[CH;D3;+0:2](-[OH;D1;+0:1])-[c:3](:[c:4]):[c:5] | 73 | [{"value": 73.0, "product": "OC(C(=O)O)C1=CC=C(C=C1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 7.5 | CELSIUS | 24 | HOUR | To a mixture of lithium chloride (17.0 g, 418 mmol), potassium hydroxide (44.9 g, 800 mmol) and ice (150 g) was added a solution of bromoform (17.5 mL, 200 mmol) and 4-isopropyl benzaldehyde (30.3 mL, 200 mmol) in 1,4-dioxane (150 mL) at 0° C., and the mixture was stirred at 5-10° C. for 24 hours and then stirred at 35... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid.Secondary alcohol | null | null | c1ccccc1 | null | null | 7.5 | 24 | CC(C)c1ccc(C=O)cc1.[OH-]>>CC(C)c1ccc(C(O)C(=O)O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4bc535bc95c94d88b2c7233959430bd8 | CC(C)c1ccc(C(O)C(=O)O)cc1.Cc1cc(C)c(C)c(O)c1>>Cc1cc(C)c2c(c1C)OC(=O)C2c1ccc(C(C)C)cc1 | S(O)(O)(=O)=O.OC(C(=O)O)C1=CC=C(C=C1)C(C)C.CC1=C(C=C(C=C1C)C)O>>C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=CC(=C2C)C)C)=O | O[CH:13]([C:11]([OH:10])=[O:12])[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22]1.O[c:7]1[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[c:8]1[CH3:9]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH3:9])[O:10][C:11](=[O:12])[CH:13]2[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22]... | CC(C)c1ccc(C(O)C(=O)O)cc1.Cc1cc(C)c(C)c(O)c1 | Cc1cc(C)c2c(c1C)OC(=O)C2c1ccc(C(C)C)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | a36a17d3b5a98a14927a5ab2b0be42d209b866ef66a0bb2bbf9dcb43cad4f8d7 | 908e0f9e50a05a6374ff137c29a63b494c9fdcd7afae396ae828385ea73c4999 | O=C1Oc2ccccc2C1c1ccccc1 | O-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7].O-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[c:10](-[C;D1;H3:11]):[c:12]:[c:13]:[c:14]:1-[C;D1;H3:15]>>[C;D1;H3:11]-[c:10]1:[c:12]:[c:13]:[c:14](-[C;D1;H3:15]):[c;H0;D3;+0:8]2:[c;H0;D3;+0:9]:1-[CH;D3;+0:1](-[c:5](:[c:6]):[c:7])-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-... | 65 | [{"value": 65.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=CC(=C2C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 115 | CELSIUS | 12 | HOUR | To a mixture of hydroxy(4-isopropylphenyl)acetic acid synthesized in Reference Example 1 (11.8 g, 60.8 mmol) and 2,3,5-trimethylphenol (12.4 g, 91.2 mmol) was added 70% sulfuric acid (10 mL) at room temperature, and the mixture was stirred at 115° C. for 12 hours. The mixture was added to water and was extracted with d... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol.Aromatic alcohol | Ester | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | O | 115 | 12 | CC(C)c1ccc(C(O)C(=O)O)cc1.Cc1cc(C)c(C)c(O)c1>O>Cc1cc(C)c2c(c1C)OC(=O)C2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc955fdcc913432a83d75d1cbc759b22 | CC(C)c1ccc(C(O)C(=O)O)cc1.Cc1cccc(O)c1C>>Cc1ccc2c(c1C)OC(=O)C2c1ccc(C(C)C)cc1 | OC(C(=O)O)C1=CC=C(C=C1)C(C)C.CC1=C(C=CC=C1C)O>>C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C=CC(=C2C)C)=O | O[C:10](=[O:11])[CH:12](O)[c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([OH:9])[c:7]1[CH3:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([c:7]1[CH3:8])[O:9][C:10](=[O:11])[CH:12]2[c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1 | CC(C)c1ccc(C(O)C(=O)O)cc1.Cc1cccc(O)c1C | Cc1ccc2c(c1C)OC(=O)C2c1ccc(C(C)C)cc1 | null | null | CO | Acylation | OtherReaction | a9a5b73428c6cee8742382adf23f6cccf5c4cf75079871710fa49d52d876205d | 7c7c21ef6846a89a0c7e34038d2f8c5934b71c90169d827b6b3d7f9d687374a5 | O=C1Oc2ccccc2C1c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-O)-[c:4](:[c:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](:[c:11]:[c:12])-[CH;D3;+0:3]-1-[c:4](:[c:5]):[c:6] | 44 | [{"value": 44.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C=CC(=C2C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using hydroxy(4-isopropylphenyl)acetic acid synthesized in Reference Example 1 and 2,3-dimethylphenol, the title compound was synthesized in the same manner as in Reference Example 2. Yield 44%. Melting point: 58-60° C. (methanol).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol.Aromatic alcohol | Ester | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | CO | null | null | CC(C)c1ccc(C(O)C(=O)O)cc1.Cc1cccc(O)c1C>CO>Cc1ccc2c(c1C)OC(=O)C2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ac38c1facb84f86b9199d8773e793b9 | CC(C)c1ccc(C(O)C(=O)O)cc1.Cc1cc(C)cc(O)c1>>Cc1cc(C)c2c(c1)OC(=O)C2c1ccc(C(C)C)cc1 | OC(C(=O)O)C1=CC=C(C=C1)C(C)C.CC=1C=C(C=C(C1)C)O>>C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=CC(=C2)C)C)=O | O[CH:12]([C:10]([OH:9])=[O:11])[c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1.O[c:7]1[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:8]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([cH:8]1)[O:9][C:10](=[O:11])[CH:12]2[c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1 | CC(C)c1ccc(C(O)C(=O)O)cc1.Cc1cc(C)cc(O)c1 | Cc1cc(C)c2c(c1)OC(=O)C2c1ccc(C(C)C)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | a36a17d3b5a98a14927a5ab2b0be42d209b866ef66a0bb2bbf9dcb43cad4f8d7 | 908e0f9e50a05a6374ff137c29a63b494c9fdcd7afae396ae828385ea73c4999 | O=C1Oc2ccccc2C1c1ccccc1 | O-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7].O-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[c:12](-[C;D1;H3:13]):[cH;D2;+0:14]:1>>[C;D1;H3:13]-[c:12]1:[c:11]:[c:10]:[c:9]:[c;H0;D3;+0:8]2:[c;H0;D3;+0:14]:1-[CH;D3;+0:1](-[c:5](:[c:6]):[c:7])-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-2 | 45 | [{"value": 45.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=CC(=C2)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using hydroxy(4-isopropylphenyl)acetic acid synthesized in Reference Example 1 and 3,5-dimethylphenol, the title compound was synthesized in the same manner as in Reference Example 2. Yield 45%. Melting point: 76-77° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol.Aromatic alcohol | Ester | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | C(C)(=O)OCC.CCCCCC | null | null | CC(C)c1ccc(C(O)C(=O)O)cc1.Cc1cc(C)cc(O)c1>C(C)(=O)OCC.CCCCCC>Cc1cc(C)c2c(c1)OC(=O)C2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c742566f1151421f8fc9dceb5b8cab0d | CC(C)c1ccc(C(O)C(=O)O)cc1.Oc1ccc(Br)cc1>>CC(C)c1ccc(C2C(=O)Oc3ccc(Br)cc32)cc1 | OC(C(=O)O)C1=CC=C(C=C1)C(C)C.BrC1=CC=C(C=C1)O>>BrC=1C=CC2=C(C(C(O2)=O)C2=CC=C(C=C2)C(C)C)C1 | O[CH:8]([c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:20][cH:19]1)[C:9](O)=[O:10].[OH:11][c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[C:9](=[O:10])[O:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]32)[cH:19][cH:20]1 | CC(C)c1ccc(C(O)C(=O)O)cc1.Oc1ccc(Br)cc1 | CC(C)c1ccc(C2C(=O)Oc3ccc(Br)cc32)cc1 | null | null | CO | Acylation | OtherReaction | a9a5b73428c6cee8742382adf23f6cccf5c4cf75079871710fa49d52d876205d | 7c7c21ef6846a89a0c7e34038d2f8c5934b71c90169d827b6b3d7f9d687374a5 | O=C1Oc2ccccc2C1c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-O)-[c:4](:[c:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](:[c:11]:[c:12])-[CH;D3;+0:3]-1-[c:4](:[c:5]):[c:6] | 30 | [{"value": 30.0, "product": "BrC=1C=CC2=C(C(C(O2)=O)C2=CC=C(C=C2)C(C)C)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using hydroxy(4-isopropylphenyl)acetic acid synthesized in Reference Example 1 and 4-bromophenol, the title compound was synthesized in the same manner as in Reference Example 2. Yield 30%. Melting point: 157-158° C. (methanol).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol.Aromatic alcohol | Ester | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | CO | null | null | CC(C)c1ccc(C(O)C(=O)O)cc1.Oc1ccc(Br)cc1>CO>CC(C)c1ccc(C2C(=O)Oc3ccc(Br)cc32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6bdb09d3125a4f06bb2a77dcbd47cfc5 | CI.Cc1cc(C)c2c(c1C)OC(=O)C2c1ccc(C(C)C)cc1>>Cc1cc(C)c2c(c1C)OC(=O)C2(C)c1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=CC(=C2C)C)C)=O.CI.[H-].[Na+].O>>C(C)(C)C1=CC=C(C=C1)C1(C(OC2=C1C(=CC(=C2C)C)C)=O)C | I[CH3:14].[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH3:9])[O:10][C:11](=[O:12])[CH:13]2[c:15]1[cH:16][cH:17][c:18]([CH:19]([CH3:20])[CH3:21])[cH:22][cH:23]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH3:9])[O:10][C:11](=[O:12])[C:13]2([CH3:14])[c:15]1[cH:16][cH:17][c:18]([CH:19]([CH3:20])[CH3:21])... | CI.Cc1cc(C)c2c(c1C)OC(=O)C2c1ccc(C(C)C)cc1 | Cc1cc(C)c2c(c1C)OC(=O)C2(C)c1ccc(C(C)C)cc1 | null | null | CN(C)C=O | C-C Coupling | Methylation with MeI_tertiary | 2df58dbc7598f4dd7d1f88d398506f8000fc8f56173da0fda4f1729c49cd7825 | 49d6f28766066d07dffbcc6f4da77792f6ba67b4de619800bad651525d6fe2e7 | O=C1Oc2ccccc2C1c1ccccc1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3]1-[#8:4]-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[c:9](:[c:10]):[c:11]>>[CH3;D1;+0:1]-[C;H0;D4;+0:8]1(-[c:9](:[c:10]):[c:11])-[C:3](=[O;D1;H0:2])-[#8:4]-[c:5]:[c:6]-1:[c:7] | 94 | [{"value": 94.0, "product": "C(C)(C)C1=CC=C(C=C1)C1(C(OC2=C1C(=CC(=C2C)C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 3-(4-isopropylphenyl)-4,6,7-trimethyl-1-benzofuran-2(3H)-one synthesized in Reference Example 2 (2.10 g, 7.13 mmol) in DMF (30 mL) was added sodium hydride (a 60% fluidized paraffin dispersion, 314 mg, 7.84 mmol) at 0° C., and the mixture was stirred at room temperature for 30 minutes. To the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HI | CN(C)C=O | null | 0.5 | CI.Cc1cc(C)c2c(c1C)OC(=O)C2c1ccc(C(C)C)cc1>CN(C)C=O>Cc1cc(C)c2c(c1C)OC(=O)C2(C)c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38992cda04e74b71804393b32ed6a00d | Cc1cc(C)c2c(c1)OC(=O)C2c1ccc(C(C)C)cc1>>Cc1cc(C)c(C(CO)c2ccc(C(C)C)cc2)c(O)c1 | C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=CC(=C2)C)C)=O>>OCC(C1=CC=C(C=C1)C(C)C)C1=C(C=C(C=C1C)C)O | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:19]([cH:21]1)[O:20][C:8](=[O:9])[CH:7]2[c:10]1[cH:11][cH:12][c:13]([CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH:7]([CH2:8][OH:9])[c:10]2[cH:11][cH:12][c:13]([CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]2)[c:19]([OH:20])[cH:21]1 | Cc1cc(C)c2c(c1)OC(=O)C2c1ccc(C(C)C)cc1 | Cc1cc(C)c(C(CO)c2ccc(C(C)C)cc2)c(O)c1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | da0d3c7a3eeadda28a29d228ff8f103888c428bfcfc295782d2b1143ff8ed39e | bb621eee13e64a87401761367bc299c7ba93ca9330953c6249ee208fbd91494f | c1ccc(Cc2ccccc2)cc1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]-[C:7]-1-[c:8]>>[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]-[C:7](-[c:8])-[CH2;D2;+0:2]-[OH;D1;+0:1] | 93 | [{"value": 93.0, "product": "OCC(C1=CC=C(C=C1)C(C)C)C1=C(C=C(C=C1C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-4,6-dimethyl-1-benzofuran-2(3H)-one synthesized in Reference Example 4, the title compound was synthesized in the same manner as in Reference Example 8. Yield 93%. Melting point: 101-102° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: synthesized in Refe... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol.Aromatic alcohol | c1ccc2c(c1)CCO2 | null | c1ccccc1.c1ccccc1 | null | C(C)(=O)OCC.CCCCCC | null | null | Cc1cc(C)c2c(c1)OC(=O)C2c1ccc(C(C)C)cc1>C(C)(=O)OCC.CCCCCC>Cc1cc(C)c(C(CO)c2ccc(C(C)C)cc2)c(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5564278b039e40dd9c6990ea070e14f7 | Cc1cc(C)c2c(c1C)OC(=O)C2(C)c1ccc(C(C)C)cc1>>Cc1cc(C)c(C(C)(CO)c2ccc(C(C)C)cc2)c(O)c1C | C(C)(C)C1=CC=C(C=C1)C1(C(OC2=C1C(=CC(=C2C)C)C)=O)C>>OCC(C)(C1=CC=C(C=C1)C(C)C)C1=C(C(=C(C=C1C)C)C)O | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:20]([c:22]1[CH3:23])[O:21][C:9](=[O:10])[C:7]2([CH3:8])[c:11]1[cH:12][cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([C:7]([CH3:8])([CH2:9][OH:10])[c:11]2[cH:12][cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]2)[c:20]([OH:21... | Cc1cc(C)c2c(c1C)OC(=O)C2(C)c1ccc(C(C)C)cc1 | Cc1cc(C)c(C(C)(CO)c2ccc(C(C)C)cc2)c(O)c1C | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | da0d3c7a3eeadda28a29d228ff8f103888c428bfcfc295782d2b1143ff8ed39e | bb621eee13e64a87401761367bc299c7ba93ca9330953c6249ee208fbd91494f | c1ccc(Cc2ccccc2)cc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[c:4]:[c:5](:[c:6])-[O;H0;D2;+0:7]-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C;D1;H3:1]-[C:2](-[c:3])(-[CH2;D2;+0:8]-[OH;D1;+0:9])-[c:4]:[c:5](-[OH;D1;+0:7]):[c:6] | 83 | [{"value": 83.0, "product": "OCC(C)(C1=CC=C(C=C1)C(C)C)C1=C(C(=C(C=C1C)C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-3,4,6,7-tetramethyl-1-benzofuran-2(3H)-one synthesized in Reference Example 6, the title compound was synthesized in the same manner as in Reference Example 8. Yield 83%. Melting point: 116-117° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: synthesized ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol.Aromatic alcohol | c1ccc2c(c1)CCO2 | null | c1ccccc1.c1ccccc1 | null | C(C)(=O)OCC.CCCCCC | null | null | Cc1cc(C)c2c(c1C)OC(=O)C2(C)c1ccc(C(C)C)cc1>C(C)(=O)OCC.CCCCCC>Cc1cc(C)c(C(C)(CO)c2ccc(C(C)C)cc2)c(O)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36071a950ced47cc9b3a73d604d452bd | Cc1cc(C)c(C(CO)c2ccc(C(C)C)cc2)c(O)c1C>>Cc1cc(C)c2c(c1C)OCC2c1ccc(C(C)C)cc1 | OCC(C1=CC=C(C=C1)C(C)C)C1=C(C(=C(C=C1C)C)C)O.N(=NC(=O)OCC)C(=O)OCC.C1(=CC=CC=C1)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=CC(=C2C)C)C | O[CH2:11][CH:12]([c:6]1[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[c:8]([CH3:9])[c:7]1[OH:10])[c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH3:9])[O:10][CH2:11][CH:12]2[c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1 | Cc1cc(C)c(C(CO)c2ccc(C(C)C)cc2)c(O)c1C | Cc1cc(C)c2c(c1C)OCC2c1ccc(C(C)C)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether (intramolecular) | 08fe01f624cfc4673e7c832ce270800ddccb38ff76736dab6575edf463f51b05 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(C2COc3ccccc32)cc1 | O-[CH2;D2;+0:1]-[C:2](-[c:3])-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]>>[c:3]-[C:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:5](:[c:7]):[c:4]-1 | 84 | [{"value": 84.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=CC(=C2C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-(2-hydroxy-1-(4-isopropylphenyl)ethyl)-3,5,6-trimethylphenol obtained in Reference Example 8 (7.85 g, 26.3 mmol) and triphenylphosphine (7.58 g, 28.9 mmol) in THF (60 mL) was added diethyl azodicarboxylate (a 40% toluene solution, 12.6 g, 28.9 mmol) with ice-cooling, and the mixture was stirred at ro... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | C1CCOC1 | null | 1 | Cc1cc(C)c(C(CO)c2ccc(C(C)C)cc2)c(O)c1C>C1CCOC1>Cc1cc(C)c2c(c1C)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-628effa69f664d04b48453bd2748c606 | Cc1ccc(C(CO)c2ccc(C(C)C)cc2)c(O)c1C>>Cc1ccc2c(c1C)OCC2c1ccc(C(C)C)cc1 | OCC(C1=CC=C(C=C1)C(C)C)C1=CC=C(C(=C1O)C)C>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C=CC(=C2C)C | O[CH2:10][CH:11]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:7]([CH3:8])[c:6]1[OH:9])[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([c:7]1[CH3:8])[O:9][CH2:10][CH:11]2[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1 | Cc1ccc(C(CO)c2ccc(C(C)C)cc2)c(O)c1C | Cc1ccc2c(c1C)OCC2c1ccc(C(C)C)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether (intramolecular) | 08fe01f624cfc4673e7c832ce270800ddccb38ff76736dab6575edf463f51b05 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(C2COc3ccccc32)cc1 | O-[CH2;D2;+0:1]-[C:2](-[c:3])-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]>>[c:3]-[C:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:5](:[c:7]):[c:4]-1 | 80 | [{"value": 80.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C=CC(=C2C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 6-(2-hydroxy-1-(4-isopropylphenyl)ethyl)-2,3-dimethylphenol synthesized in Reference Example 9, the title compound was synthesized in the same manner as in Reference Example 13. Yield 80%. Melting point: 50-51° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: synthesized in Reference Examp... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | CO | null | null | Cc1ccc(C(CO)c2ccc(C(C)C)cc2)c(O)c1C>CO>Cc1ccc2c(c1C)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0fb32881f4354a9789f966d985b1b45a | Cc1cc(C)c(C(CO)c2ccc(C(C)C)cc2)c(O)c1>>Cc1cc(C)c2c(c1)OCC2c1ccc(C(C)C)cc1 | OCC(C1=CC=C(C=C1)C(C)C)C1=C(C=C(C=C1C)C)O>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=CC(=C2)C)C | O[CH2:10][CH:11]([c:6]1[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:8][c:7]1[OH:9])[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([cH:8]1)[O:9][CH2:10][CH:11]2[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1 | Cc1cc(C)c(C(CO)c2ccc(C(C)C)cc2)c(O)c1 | Cc1cc(C)c2c(c1)OCC2c1ccc(C(C)C)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether (intramolecular) | 08fe01f624cfc4673e7c832ce270800ddccb38ff76736dab6575edf463f51b05 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(C2COc3ccccc32)cc1 | O-[CH2;D2;+0:1]-[C:2](-[c:3])-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]>>[c:3]-[C:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:5](:[c:7]):[c:4]-1 | 85 | [{"value": 85.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=CC(=C2)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2-(2-hydroxy-1-(4-isopropylphenyl)ethyl)-3,5-dimethylphenol synthesized in Reference Example 10, the title compound was synthesized in the same manner as in Reference Example 13. Yield 85%. Melting point: 46-47° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: synthesized in Reference Exam... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | CO | null | null | Cc1cc(C)c(C(CO)c2ccc(C(C)C)cc2)c(O)c1>CO>Cc1cc(C)c2c(c1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78f320e788624654b9df79edd1721746 | CC(C)c1ccc(C(CO)c2cc(Br)ccc2O)cc1>>CC(C)c1ccc(C2COc3ccc(Br)cc32)cc1 | BrC1=CC(=C(C=C1)O)C(CO)C1=CC=C(C=C1)C(C)C>>BrC=1C=CC2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1 | O[CH2:9][CH:8]([c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:19][cH:18]1)[c:17]1[c:11]([OH:10])[cH:12][cH:13][c:14]([Br:15])[cH:16]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][O:10][c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]32)[cH:18][cH:19]1 | CC(C)c1ccc(C(CO)c2cc(Br)ccc2O)cc1 | CC(C)c1ccc(C2COc3ccc(Br)cc32)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether (intramolecular) | 08fe01f624cfc4673e7c832ce270800ddccb38ff76736dab6575edf463f51b05 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(C2COc3ccccc32)cc1 | O-[CH2;D2;+0:1]-[C:2](-[c:3])-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]>>[c:7]:[c:5]1:[c:4]-[C:2](-[c:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-1 | 62 | [{"value": 62.0, "product": "BrC=1C=CC2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 4-bromo-2-(2-hydroxy-1-(4-isopropylphenyl)ethyl)phenol synthesized in Reference Example 11, the title compound was synthesized in the same manner as in Reference Example 13. Yield 62%. Melting point: 90-91° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: synthesized in Reference Example 1... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | CO | null | null | CC(C)c1ccc(C(CO)c2cc(Br)ccc2O)cc1>CO>CC(C)c1ccc(C2COc3ccc(Br)cc32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ed47b445b744e1f84ecf4da64e12ce0 | BrBr.Cc1cc(C)c2c(c1C)OCC2c1ccc(C(C)C)cc1>>Cc1c(C)c2c(c(C)c1Br)C(c1ccc(C(C)C)cc1)CO2 | BrBr.C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=CC(=C2C)C)C.O.C(C)(=O)[O-].[Na+]>>BrC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C | Br[Br:10].[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[cH:9]1)[CH:11]([c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1)[CH2:21][O:22]2>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[Br:10])[CH:11]([c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1)[CH2:21][... | BrBr.Cc1cc(C)c2c(c1C)OCC2c1ccc(C(C)C)cc1 | Cc1c(C)c2c(c(C)c1Br)C(c1ccc(C(C)C)cc1)CO2 | null | null | C(C)#N | Functional Group Interconversion | Bromination | 8a5899f39c577ae2f5dbb7e89484f9814910050aa00e810b5c8bafb1acd06dbc | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(C2COc3ccccc32)cc1 | Br-[Br;H0;D1;+0:1].[C;D1;H3:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[C;D1;H3:7]):[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:3](-[C;D1;H3:2]):[c:4]):[c:6](-[C;D1;H3:7]):[c:8] | 99 | [{"value": 99.0, "product": "BrC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of 3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran synthesized in Reference Example 13 (6.10 g, 21.8 mmol) and sodium acetate (1.97 g, 24.0 mmol) in acetonitrile (30 mL) was added bromine (1.17 mL, 22.9 mmol), and the mixture was stirred at the same temperature for 1 hour. Water was poured i... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HBr | C(C)#N | null | 1 | BrBr.Cc1cc(C)c2c(c1C)OCC2c1ccc(C(C)C)cc1>C(C)#N>Cc1c(C)c2c(c(C)c1Br)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72240799120b43f39ccf3ee7fbeb78a0 | Cc1c(Br)cc2c(c1C)OC(=O)C2(C)c1ccc(C(C)C)cc1>>Cc1c(Br)cc(C(C)(CO)c2ccc(C(C)C)cc2)c(O)c1C | BrC=1C(=C(C2=C(C(C(O2)=O)(C)C2=CC=C(C=C2)C(C)C)C1)C)C>>BrC1=C(C(=C(C(=C1)C(CO)(C)C1=CC=C(C=C1)C(C)C)O)C)C | [CH3:1][c:2]1[c:3]([Br:4])[cH:5][c:6]2[c:20]([c:22]1[CH3:23])[O:21][C:9](=[O:10])[C:7]2([CH3:8])[c:11]1[cH:12][cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]1>>[CH3:1][c:2]1[c:3]([Br:4])[cH:5][c:6]([C:7]([CH3:8])([CH2:9][OH:10])[c:11]2[cH:12][cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]2)[c:20]([OH:21])... | Cc1c(Br)cc2c(c1C)OC(=O)C2(C)c1ccc(C(C)C)cc1 | Cc1c(Br)cc(C(C)(CO)c2ccc(C(C)C)cc2)c(O)c1C | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | da0d3c7a3eeadda28a29d228ff8f103888c428bfcfc295782d2b1143ff8ed39e | bb621eee13e64a87401761367bc299c7ba93ca9330953c6249ee208fbd91494f | c1ccc(Cc2ccccc2)cc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[c:4]:[c:5](:[c:6])-[O;H0;D2;+0:7]-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C;D1;H3:1]-[C:2](-[c:3])(-[CH2;D2;+0:8]-[OH;D1;+0:9])-[c:4]:[c:5](-[OH;D1;+0:7]):[c:6] | 83 | [{"value": 83.0, "product": "BrC1=C(C(=C(C(=C1)C(CO)(C)C1=CC=C(C=C1)C(C)C)O)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 5-bromo-3-(4-isopropylphenyl)-3,6,7-trimethyl-1-benzofuran-2(3H)-one synthesized in Reference Example 21, the title compound was synthesized in the same manner as in Reference Example 8. Yield 83%. Melting point: 110-111° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: synthes... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol.Aromatic alcohol | c1ccc2c(c1)CCO2 | null | c1ccccc1.c1ccccc1 | null | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(Br)cc2c(c1C)OC(=O)C2(C)c1ccc(C(C)C)cc1>C(C)(=O)OCC.CCCCCC>Cc1c(Br)cc(C(C)(CO)c2ccc(C(C)C)cc2)c(O)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e203dee6114543f08770ce76990bd0d0 | Cc1c(C)c2c(c(C)c1Br)C(c1ccc(C(C)C)cc1)CO2.NCc1ccccc1>>Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccc(C(C)C)cc1)CO2 | BrC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C.O.C(C1=CC=CC=C1)N.CC(C)([O-])C.[Na+]>>C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C | Br[c:9]1[c:2]([CH3:1])[c:3]([CH3:4])[c:5]2[c:6]([c:7]1[CH3:8])[CH:18]([c:19]1[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]1)[CH2:28][O:29]2.[NH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][... | Cc1c(C)c2c(c(C)c1Br)C(c1ccc(C(C)C)cc1)CO2.NCc1ccccc1 | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccc(C(C)C)cc1)CO2 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8 | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 3eefa8c0242a0dbc67760ed46fbbe572c7b05262288867a6644b519cc5731092 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccc3c(c2)C(c2ccccc2)CO3)cc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](-[C;D1;H3:6]):[c:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[C;D1;H3:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]-[c:10]):[c:5](-[C;D1;H3:6]):[c:7] | 91 | [{"value": 91.0, "product": "C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 5-bromo-3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran obtained in Reference Example 18 (920 mg, 2.56 mmol) and benzylamine (0.34 mL, 3.07 mmol) in toluene (10 mL), were added palladium acetate (6 mg, 0.03 mmol) and BINAP (48 mg, 0.09 mmol) at room temperature, and the mixture was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCO2 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8.C1(=CC=CC=C1)C | null | 0.25 | Cc1c(C)c2c(c(C)c1Br)C(c1ccc(C(C)C)cc1)CO2.NCc1ccccc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8.C1(=CC=CC=C1)C>Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ebf80d70ffce43bea7334ade08b99f29 | Cc1c(Br)cc(C(C)(CO)c2ccc(C(C)C)cc2)c(O)c1C>>Cc1c(Br)cc2c(c1C)OCC2(C)c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C(=C1)C(CO)(C)C1=CC=C(C=C1)C(C)C)O)C)C.N(=NC(=O)OCC)C(=O)OCC.C1(=CC=CC=C1)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrC=1C(=C(C2=C(C(CO2)(C)C2=CC=C(C=C2)C(C)C)C1)C)C | O[CH2:11][C:12]([c:6]1[cH:5][c:3]([Br:4])[c:2]([CH3:1])[c:8]([CH3:9])[c:7]1[OH:10])([CH3:13])[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22]1>>[CH3:1][c:2]1[c:3]([Br:4])[cH:5][c:6]2[c:7]([c:8]1[CH3:9])[O:10][CH2:11][C:12]2([CH3:13])[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22... | Cc1c(Br)cc(C(C)(CO)c2ccc(C(C)C)cc2)c(O)c1C | Cc1c(Br)cc2c(c1C)OCC2(C)c1ccc(C(C)C)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether (intramolecular) | 08fe01f624cfc4673e7c832ce270800ddccb38ff76736dab6575edf463f51b05 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(C2COc3ccccc32)cc1 | O-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[c:4])-[c:5]:[c:6](-[OH;D1;+0:7]):[c:8]>>[C;D1;H3:3]-[C:2]1(-[c:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:6](:[c:8]):[c:5]-1 | null | [] | null | null | 1 | HOUR | To a solution of 4-bromo-6-(2-hydroxy-1-(4-isopropylphenyl)-1-methylethyl)-2,3-dimethylphenol obtained in Reference Example 22 (830 mg, 2.21 mmol) and triphenylphosphine (638 mg, 2.43 mmol) in THF (60 mL) was added diethyl azodicarboxylate (a 40% toluene solution, 1.06 g, 2.43 mmol) with ice-cooling, and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | C1CCOC1 | null | 1 | Cc1c(Br)cc(C(C)(CO)c2ccc(C(C)C)cc2)c(O)c1C>C1CCOC1>Cc1c(Br)cc2c(c1C)OCC2(C)c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-347826c140b148cbaa952a0c62b9a9c0 | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)C)cc1)CO2 | C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C.C(=O)[O-].[NH4+]>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N)C | c1ccc(C[NH:10][c:9]2[c:2]([CH3:1])[c:3]([CH3:4])[c:5]3[c:6]([c:7]2[CH3:8])[CH:11]([c:12]2[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]2)[CH2:21][O:22]3)cc1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH2:10])[CH:11]([c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1)[... | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)C)cc1)CO2 | null | [C].[Pd] | C(C)O | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(C2COc3ccccc32)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 74 | [{"value": 74.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N-benzyl-3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 24 (900 mg, 2.33 mmol), 10%-palladium carbon (50% hydrous, 90 mg) and ammonium formate (294 mg, 4.66 mmol) in ethanol (10 mL) was heated under reflux for 2 hours. The solid material was removed and... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | [C].[Pd].C(C)O | null | null | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccc(C(C)C)cc1)CO2>[C].[Pd].C(C)O>Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a303b20a472c4e51902ab574154039c7 | CCOC(=O)C(C)(C)Br.Cc1cccc(O)c1C>>CCOC(=O)C(C)(C)Oc1cccc(C)c1C | O.CC1=C(C=CC=C1C)O.BrC(C(=O)OCC)(C)C.C([O-])([O-])=O.[K+].[K+]>>CC1=C(OC(C(=O)OCC)(C)C)C=CC=C1C | Br[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8].[OH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([CH3:15])[c:16]1[CH3:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:12][cH:13][c:14]([CH3:15])[c:16]1[CH3:17] | CCOC(=O)C(C)(C)Br.Cc1cccc(O)c1C | CCOC(=O)C(C)(C)Oc1cccc(C)c1C | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 657b1e065fabda84e4d6cc80f4d94ce754af0792c9117981e41887a4384f6981 | 2495a256265ef36132d409a6a3e2bd04c3acda5f236d910f184b0a36a846defe | c1ccccc1 | Br-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | 36 | HOUR | To a solution of 2,3-dimethylphenol (25.0 g, 205 mmol) in dimethylsulfoxide (200 mL) were added ethyl 2-bromo-isobutyrate (60 mL, 409 mmol) and potassium carbonate (56.5 g, 409 mmol) at room temperature, and the mixture was stirred for 36 hours. Water was added to the reaction solution and the mixture was extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | CS(=O)C | null | 36 | CCOC(=O)C(C)(C)Br.Cc1cccc(O)c1C>CS(=O)C>CCOC(=O)C(C)(C)Oc1cccc(C)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6ce2883d770d4f568bd1cdc173c6f12e | Cc1cccc(OC(C)(C)C(=O)O)c1C>>Cc1ccc2c(c1C)OC(C)(C)C2=O | CC1=C(OC(C(=O)O)(C)C)C=CC=C1C.[Cl-].[Al+3].[Cl-].[Cl-].CN(C)C=O.C(C(=O)Cl)(=O)Cl>>CC1(OC2=C(C1=O)C=CC(=C2C)C)C | O[C:13]([C:10]([O:9][c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:7]1[CH3:8])([CH3:11])[CH3:12])=[O:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([c:7]1[CH3:8])[O:9][C:10]([CH3:11])([CH3:12])[C:13]2=[O:14] | Cc1cccc(OC(C)(C)C(=O)O)c1C | Cc1ccc2c(c1C)OC(C)(C)C2=O | null | null | O.C1CCOC1 | Functional Group Interconversion | OtherReaction | 07c0617fba4b5b8b4f6e211c6b50ebf5bf60539aad6b1d235a93c13cf5d42336 | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1COc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[C;D1;H3:4]-[C:3]1(-[C;D1;H3:5])-[#8:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](:[c:10]:[c:11])-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | 71 | [{"value": 71.0, "product": "CC1(OC2=C(C1=O)C=CC(=C2C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-(2,3-dimethylphenoxy)-2-methylpropionic acid obtained in Reference Example 36 (21.0 g, 101 mmol) in THF (200 mL) was added DMF (0.1 mL), and then to the mixture was added dropwise oxalyl chloride (10.6 mL, 121 mmol). The reaction solution was warmed to room temperature, stirred for 1 hour, and then c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | HO- | O.C1CCOC1 | null | 1 | Cc1cccc(OC(C)(C)C(=O)O)c1C>O.C1CCOC1>Cc1ccc2c(c1C)OC(C)(C)C2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b16d625f2845495d85c3041906b21fcb | Cc1cc(OC(C)(C)C(=O)O)cc(C)c1C>>Cc1cc2c(c(C)c1C)C(=O)C(C)(C)O2 | CC=1C=C(OC(C(=O)O)(C)C)C=C(C1C)C>>CC1(OC2=C(C1=O)C(=C(C(=C2)C)C)C)C | O[C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[O:15][c:4]1[cH:3][c:2]([CH3:1])[c:8]([CH3:9])[c:6]([CH3:7])[cH:5]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[CH3:9])[C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[O:15]2 | Cc1cc(OC(C)(C)C(=O)O)cc(C)c1C | Cc1cc2c(c(C)c1C)C(=O)C(C)(C)O2 | null | null | CCCCCC | Functional Group Interconversion | OtherReaction | 07c0617fba4b5b8b4f6e211c6b50ebf5bf60539aad6b1d235a93c13cf5d42336 | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1COc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10](-[C;D1;H3:11]):[c:12]>>[C;D1;H3:4]-[C:3]1(-[C;D1;H3:5])-[#8:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](:[c:10](-[C;D1;H3:11]):[c:12])-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | 90 | [{"value": 90.0, "product": "CC1(OC2=C(C1=O)C(=C(C(=C2)C)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2-(3,4,5-trimethyl phenoxy)-2-methylpropionic acid obtained in Reference Example 40, the title compound was synthesized in the same manner as in Reference Example 41. Yield 90%. Melting point: 77-78° C. (hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Example 40 | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | HO- | CCCCCC | null | null | Cc1cc(OC(C)(C)C(=O)O)cc(C)c1C>CCCCCC>Cc1cc2c(c(C)c1C)C(=O)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bf5133e21aff459ca5e01da7ef38cae1 | Cc1c([N+](=O)[O-])cc2c(c1C)OC(C)(C)C2=O>>Cc1c(N)cc2c(c1C)OC(C)(C)C2=O | CC1(OC2=C(C1=O)C=C(C(=C2C)C)[N+](=O)[O-])C.C(=O)[O-].[NH4+]>>NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1)C)C | O=[N+:4]([O-])[c:3]1[c:2]([CH3:1])[c:8]([CH3:9])[c:7]2[c:6]([cH:5]1)[C:14](=[O:15])[C:11]([CH3:12])([CH3:13])[O:10]2>>[CH3:1][c:2]1[c:3]([NH2:4])[cH:5][c:6]2[c:7]([c:8]1[CH3:9])[O:10][C:11]([CH3:12])([CH3:13])[C:14]2=[O:15] | Cc1c([N+](=O)[O-])cc2c(c1C)OC(C)(C)C2=O | Cc1c(N)cc2c(c1C)OC(C)(C)C2=O | null | [C].[Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1COc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 92 | [{"value": 92.0, "product": "NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2,2,6,7-tetramethyl-5-nitro-1-benzofuran-3(2H)-one obtained in Reference Example 46 (5.0 g, 21.3 mmol), 10%-palladium carbon (50% hydrous, 500 mg) and ammonium formate (7.06 g, 85.0 mmol) in methanol (100 mL) was heated under reflux for two hours. The solid material was removed and the filtrate was concent... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CCO2 | Other | [C].[Pd].CO | null | null | Cc1c([N+](=O)[O-])cc2c(c1C)OC(C)(C)C2=O>[C].[Pd].CO>Cc1c(N)cc2c(c1C)OC(C)(C)C2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac71fe16686444ff81ae363612198b6f | Cc1cc([N+](=O)[O-])c(C)c2c1OC(C)(C)C2=O>>Cc1cc(N)c(C)c2c1OC(C)(C)C2=O | CC1(OC2=C(C1=O)C(=C(C=C2C)[N+](=O)[O-])C)C>>NC=1C=C(C2=C(C(C(O2)(C)C)=O)C1C)C | O=[N+:5]([O-])[c:4]1[cH:3][c:2]([CH3:1])[c:9]2[c:8]([c:6]1[CH3:7])[C:14](=[O:15])[C:11]([CH3:12])([CH3:13])[O:10]2>>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[c:6]([CH3:7])[c:8]2[c:9]1[O:10][C:11]([CH3:12])([CH3:13])[C:14]2=[O:15] | Cc1cc([N+](=O)[O-])c(C)c2c1OC(C)(C)C2=O | Cc1cc(N)c(C)c2c1OC(C)(C)C2=O | null | null | C(C)(=O)OCC.CCCCCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1COc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 97 | [{"value": 97.0, "product": "NC=1C=C(C2=C(C(C(O2)(C)C)=O)C1C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,4,7-tetramethyl-5-nitro-1-benzofuran-3(2H)-one obtained in Reference Example 47, the title compound was synthesized in the same manner as in Reference Example 54. Yield 97%. Melting point: 124-126° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Examp... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1cc([N+](=O)[O-])c(C)c2c1OC(C)(C)C2=O>C(C)(=O)OCC.CCCCCC>Cc1cc(N)c(C)c2c1OC(C)(C)C2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d23742b8602f40599e8257802fb962e1 | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(=O)C(C)(C)O2>>Cc1c(C)c2c(c(C)c1N)C(=O)C(C)(C)O2 | C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1C)C)C>>NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1C)C)C | c1ccc(C[NH:10][c:9]2[c:2]([CH3:1])[c:3]([CH3:4])[c:5]3[c:6]([c:7]2[CH3:8])[C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[O:16]3)cc1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH2:10])[C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[O:16]2 | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(=O)C(C)(C)O2 | Cc1c(C)c2c(c(C)c1N)C(=O)C(C)(C)O2 | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | O=C1COc2ccccc21 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 88 | [{"value": 88.0, "product": "NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 5-(benzylamino)-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-one obtained in Reference Example 52, the title compound was synthesized in the same manner as in Reference Example 30. Yield 88%. Melting point: 92-93° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Referen... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(=O)C(C)(C)O2>C(C)(=O)OCC.CCCCCC>Cc1c(C)c2c(c(C)c1N)C(=O)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-32c37e0b60494dd7b26c55a4580caac5 | Cc1c(C)c(NCc2ccccc2)c2c(c1C)C(=O)C(C)(C)O2>>Cc1c(C)c(N)c2c(c1C)C(=O)C(C)(C)O2 | C(C1=CC=CC=C1)NC1=C(C(=C(C=2C(C(OC21)(C)C)=O)C)C)C>>NC1=C(C(=C(C=2C(C(OC21)(C)C)=O)C)C)C | c1ccc(C[NH:6][c:5]2[c:3]([CH3:4])[c:2]([CH3:1])[c:9]([CH3:10])[c:8]3[c:7]2[O:16][C:13]([CH3:14])([CH3:15])[C:11]3=[O:12])cc1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]([NH2:6])[c:7]2[c:8]([c:9]1[CH3:10])[C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[O:16]2 | Cc1c(C)c(NCc2ccccc2)c2c(c1C)C(=O)C(C)(C)O2 | Cc1c(C)c(N)c2c(c1C)C(=O)C(C)(C)O2 | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | O=C1COc2ccccc21 | [#8:1]-[c:2]:[c:3](-[NH;D2;+0:4]-C-c1:c:c:c:c:c:1):[c:5]>>[#8:1]-[c:2]:[c:3](-[NH2;D1;+0:4]):[c:5] | null | [] | null | null | null | null | Using 7-(benzylamino)-2,2,4,5,6-pentamethyl-1-benzofuran-3(2H)-one obtained in Reference Example 53, the title compound was synthesized in the same manner as in Reference Example 30. Yield: quantitative. Melting point: 141-142° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtaine... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(C)c(NCc2ccccc2)c2c(c1C)C(=O)C(C)(C)O2>C(C)(=O)OCC.CCCCCC>Cc1c(C)c(N)c2c(c1C)C(=O)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1c388f8cd154e7aa4759a6e8dabdd25 | CC(C)(C)CC(=O)Cl.Cc1c(C)c2c(c(C)c1N)C(=O)C(C)(C)O2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(=O)C(C)(C)O2 | C(C)N(CC)CC.NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1C)C)C.O.C(C)(C)(C)CC(=O)Cl>>CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1C)C)C)(C)C | Cl[C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH2:10])[C:18](=[O:19])[C:20]([CH3:21])([CH3:22])[O:23]2>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:18](=[O:19])[C:... | CC(C)(C)CC(=O)Cl.Cc1c(C)c2c(c(C)c1N)C(=O)C(C)(C)O2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(=O)C(C)(C)O2 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1COc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 54 | [{"value": 54.0, "product": "CC(CC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1C)C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 5-amino-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-one obtained in Reference Example 57 (3.00 g, 13.7 mmol) and tert-butylacetyl chloride (2.03 g, 15.1 mmol) in dichloromethane (30 mL) was added triethylamine (2.3 mL, 16.4 mmol) at room temperature, and the mixture was stirred at room temperature for 30 ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCO2 | HCl | ClCCl | null | 0.5 | CC(C)(C)CC(=O)Cl.Cc1c(C)c2c(c(C)c1N)C(=O)C(C)(C)O2>ClCCl>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(=O)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4969a7af16644b7a01aa9a3133f17ea | Cc1c(C)c2c(c(C)c1N)OC(C)(C)C2=O.O=CO>>Cc1c(C)c2c(c(C)c1NC=O)OC(C)(C)C2=O | NC1=C(C2=C(C(C(O2)(C)C)=O)C(=C1C)C)C.C(=O)O>>CC1(OC2=C(C1=O)C(=C(C(=C2C)NC=O)C)C)C | [CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH2:10])[O:13][C:14]([CH3:15])([CH3:16])[C:17]2=[O:18].O[CH:11]=[O:12]>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][CH:11]=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[C:17]2=[O:18] | Cc1c(C)c2c(c(C)c1N)OC(C)(C)C2=O.O=CO | Cc1c(C)c2c(c(C)c1NC=O)OC(C)(C)C2=O | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1COc2ccccc21 | O-[CH;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6] | 81 | [{"value": 81.0, "product": "CC1(OC2=C(C1=O)C(=C(C(=C2C)NC=O)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of formic acid (5 mL) with 6-amino-2,2,4,5,7-pentamethyl-1-benzofuran-3(2H)-one (700 mg, 3.19 mmol) obtained in Reference Example 72, was heated under reflux for 5 hours. The solvent was distilled off under reduced pressure, water and ethyl acetate were added to the residue, and the aqueous layer was extracte... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCO2 | HO- | null | null | null | Cc1c(C)c2c(c(C)c1N)OC(C)(C)C2=O.O=CO>>Cc1c(C)c2c(c(C)c1NC=O)OC(C)(C)C2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d56a2f205fb14ed195d7ae398bd709e5 | CC(C)c1ccc(Br)cc1.Cc1c(NC(=O)OC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O>>Cc1c(NC(=O)OC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1ccc(C(C)C)cc1 | CC1(OC2=C(C1=O)C=C(C(=C2C)C)NC(OC(C)(C)C)=O)C.BrC1=CC=C(C=C1)C(C)C.C(CCC)[Li].CCCCCC>>OC1(C(OC2=C1C=C(C(=C2C)C)NC(OC(C)(C)C)=O)(C)C)C2=CC=C(C=C2)C(C)C | Br[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1.[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]1[CH3:16])[O:17][C:18]([CH3:19])([CH3:20])[C:21]2=[O:22]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:1... | CC(C)c1ccc(Br)cc1.Cc1c(NC(=O)OC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O | Cc1c(NC(=O)OC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1ccc(C(C)C)cc1 | null | null | O.C1CCOC1 | C-C Coupling | Grignard_alcohol | dc15c67ee64d6e57d57db2cb0f918b6b1d8338f80afda9b1c0093977e8b590e6 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc(C2COc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7]1(-[C;D1;H3:8])-[#8:9]-[c:10]:[c:11](:[c:12])-[C;H0;D3;+0:13]-1=[O;H0;D1;+0:14]>>[C;D1;H3:6]-[C:7]1(-[C;D1;H3:8])-[#8:9]-[c:10]:[c:11](:[c:12])-[C;H0;D4;+0:13]-1(-[OH;D1;+0:14])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 30 | MINUTE | To a solution of 4-bromocumene (6.25 g, 31.4 mmol) in THF (50 mL) was added dropwise a solution of n-butyllithium in hexane (1.60 M, 19.6 mL, 31.4 mmol) under arogon atmosphere at −78° C., and the mixture was stirred at the same temperature for 30 minutes. Then, to the reaction solution was added dropwise a solution of... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccc2c(c1)CCO2.c1ccccc1 | Br- | O.C1CCOC1 | null | 0.5 | CC(C)c1ccc(Br)cc1.Cc1c(NC(=O)OC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O>O.C1CCOC1>Cc1c(NC(=O)OC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9063f10311cc4914932d0286636984e3 | Cc1c(C)c2c(c(C)c1NC=O)OC(C)(C)C2=O.[Cl][Mg][CH2]c1ccccc1>>Cc1c(C)c2c(c(C)c1NC=O)OC(C)(C)C2(O)Cc1ccccc1 | O.C(C1=CC=CC=C1)[Mg]Cl.CC1(OC2=C(C1=O)C(=C(C(=C2C)NC=O)C)C)C>>C(C1=CC=CC=C1)C1(C(OC2=C1C(=C(C(=C2C)NC=O)C)C)(C)C)O | [CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][CH:11]=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[C:17]2=[O:18].[Cl][Mg][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][CH:11]=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[C:17]2([OH:18])[C... | Cc1c(C)c2c(c(C)c1NC=O)OC(C)(C)C2=O.[Cl][Mg][CH2]c1ccccc1 | Cc1c(C)c2c(c(C)c1NC=O)OC(C)(C)C2(O)Cc1ccccc1 | null | null | C1CCOC1 | C-C Coupling | Grignard from ketone to alcohol | 2dc8a1a24dc81b7eec00983b8472223608c7deab57f56f9cccd0d6ef8c288a6a | 5854166cd4ea706bc07d74dc79eb8f4a990bc6c5eacbf0ca947d88ee86e78fdf | c1ccc(CC2COc3ccccc32)cc1 | [C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[#8:4]-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9].[Cl]-[Mg]-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[#8:4]-[c:5]:[c:6](:[c:7])-[C;H0;D4;+0:8]-1(-[OH;D1;+0:9])-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13] | null | [] | null | null | 2 | HOUR | A solution of (2,2,4,5,7-pentamethyl-3-oxo-2,3-dihydro-1-benzofuran-6-yl)formamide obtained in Reference Example 73 (600 mg, 2.43 mmol) in THF (5 mL) was added dropwise to a solution of benzylmagnesium chloride (a 2.0 M THF solution, 10.0 mL, 20.0 mmol) in THF (20 mL) under argon atmosphere, and the mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | Tertiary alcohol | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | Mg | C1CCOC1 | null | 2 | Cc1c(C)c2c(c(C)c1NC=O)OC(C)(C)C2=O.[Cl][Mg][CH2]c1ccccc1>C1CCOC1>Cc1c(C)c2c(c(C)c1NC=O)OC(C)(C)C2(O)Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29548313b0fb41a0930c87c7d862c48a | Cc1c(C)c2c(c(C)c1N)C(=O)C(C)(C)O2.Cc1ccc(Br)cc1>>Cc1ccc(C2(O)c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1 | NC=1C(=C(C2=C(C(C(O2)(C)C)=O)C1C)C)C.BrC1=CC=C(C=C1)C.C(CCC)[Li].CCCCCC>>NC=1C(=C(C2=C(C(C(O2)(C)C)(O)C2=CC=C(C=C2)C)C1C)C)C | [C:6]1(=[O:7])[c:8]2[c:9]([CH3:10])[c:11]([NH2:12])[c:13]([CH3:14])[c:15]([CH3:16])[c:17]2[O:18][C:19]1([CH3:20])[CH3:21].Br[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:23][cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2([OH:7])[c:8]3[c:9]([CH3:10])[c:11]([NH2:12])[c:13]([CH3:14])[c:15]([CH3:16])[c:17]3[O:18][C:19]2([CH3:20])[CH... | Cc1c(C)c2c(c(C)c1N)C(=O)C(C)(C)O2.Cc1ccc(Br)cc1 | Cc1ccc(C2(O)c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1 | null | null | O.C1CCOC1 | C-C Coupling | Grignard_alcohol | dc15c67ee64d6e57d57db2cb0f918b6b1d8338f80afda9b1c0093977e8b590e6 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc(C2COc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7]1(-[C;D1;H3:8])-[#8:9]-[c:10]:[c:11](:[c:12])-[C;H0;D3;+0:13]-1=[O;H0;D1;+0:14]>>[C;D1;H3:6]-[C:7]1(-[C;D1;H3:8])-[#8:9]-[c:10]:[c:11](:[c:12])-[C;H0;D4;+0:13]-1(-[OH;D1;+0:14])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 65 | [{"value": 65.0, "product": "NC=1C(=C(C2=C(C(C(O2)(C)C)(O)C2=CC=C(C=C2)C)C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 4-bromotoluene (2.73 g, 16.0 mmol) in THF (30 mL) was added dropwise a solution of n-butyllithium in hexane (1.60 M, 10.0 mL, 16.0 mmol) under argon atmosphere at −78° C., and the mixture was stirred at the same temperature for 30 minutes. Then, to the reaction solution was added dropwise a solution of... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Br- | O.C1CCOC1 | null | 0.5 | Cc1c(C)c2c(c(C)c1N)C(=O)C(C)(C)O2.Cc1ccc(Br)cc1>O.C1CCOC1>Cc1ccc(C2(O)c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-10463635bd034e0bb913030ee8f322a7 | CC(C)C(=O)c1ccc(C(C)C)cc1.COc1ccccc1Br>>COc1ccccc1C(O)(c1ccc(C(C)C)cc1)C(C)C | O.C(C)(C)C1=CC=C(C=C1)C(C(C)C)=O.BrC1=C(C=CC=C1)OC.C(CCC)[Li]>>C(C)(C)C1=CC=C(C=C1)C(C(C)C)(O)C1=C(C=CC=C1)OC | [C:9](=[O:10])([c:11]1[cH:12][cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]1)[CH:20]([CH3:21])[CH3:22].Br[c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9]([OH:10])([c:11]1[cH:12][cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]1)[CH:20]([CH3:21])[CH3:... | CC(C)C(=O)c1ccc(C(C)C)cc1.COc1ccccc1Br | COc1ccccc1C(O)(c1ccc(C(C)C)cc1)C(C)C | null | null | C1CCOC1 | C-C Coupling | Grignard_alcohol | 23831eb2f5100c758a065f977b2daac4728a2009a2a7f37e9b01c50283e9e583 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc(Cc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[c:12](:[c:13]):[c:14]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D4;+0:10](-[OH;D1;+0:11])(-[C:8](-[C;D1;H3:7])-[C;D1;H3:9])-[c:12](:[c:13]):[c:14]):[c:2]:[c:3] | 43 | [{"value": 43.0, "product": "C(C)(C)C1=CC=C(C=C1)C(C(C)C)(O)C1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.7, "product": "C(C)(C)C1=CC=C(C=C1)C(C(C)C)(O)C1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 2-bromoanisole (5.0 g, 26.7 mmol) in THF (50 mL) was added n-butyllithium (1.6 M, 18 mL, 29 mmol) at −78° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction solution was added 1-(4-isopropylphenyl)-2-methylpropan-1-one (5.70 g, 30.0 mmol), and the mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | C1CCOC1 | null | 0.5 | CC(C)C(=O)c1ccc(C(C)C)cc1.COc1ccccc1Br>C1CCOC1>COc1ccccc1C(O)(c1ccc(C(C)C)cc1)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7bd353d044cb4991b15f00dce48178be | COc1ccccc1C(O)(c1ccc(C(C)C)cc1)C(C)C>>CC(C)c1ccc(C2c3ccccc3OC2(C)C)cc1 | C(C)(=O)O.C(C)(C)C1=CC=C(C=C1)C(C(C)C)(O)C1=C(C=CC=C1)OC.O.Br>>C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C=CC=C2)(C)C | C[O:15][c:14]1[c:9]([C:8](O)([c:7]2[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:20][cH:19]2)[CH:16]([CH3:17])[CH3:18])[cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[O:15][C:16]2([CH3:17])[CH3:18])[cH:19][cH:20]1 | COc1ccccc1C(O)(c1ccc(C(C)C)cc1)C(C)C | CC(C)c1ccc(C2c3ccccc3OC2(C)C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 58c1e8a6b0fb54736fce12602887392a72c98dcd612152b5c542155d025eacf0 | ba55b0723234e68b590be0c71b7a395362712495d20a4ad5682afa361fa48a3a | c1ccc(C2COc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D4;+0:5](-O)(-[CH;D3;+0:6](-[C;D1;H3:7])-[C;D1;H3:8])-[c:9](:[c:10]):[c:11]):[c:12]>>[C;D1;H3:7]-[C;H0;D4;+0:6]1(-[C;D1;H3:8])-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](:[c:12])-[CH;D3;+0:5]-1-[c:9](:[c:10]):[c:11] | 89 | [{"value": 89.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C=CC=C2)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(4-isopropylphenyl)-1-(2-methoxyphenyl)-2-methylpropan-1-ol obtained in Reference Example 82 (3.4 g, 11.4 mmol), 48% hydrobromic acid (50 mL) and acetic acid (10 mL) was heated under reflux under argon atmosphere for 16 hours. After cooling, water was added to the reaction solution, which was extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary alcohol | Ether | null | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | null | null | null | COc1ccccc1C(O)(c1ccc(C(C)C)cc1)C(C)C>>CC(C)c1ccc(C2c3ccccc3OC2(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc28da186ba54fde928140f29e5b9422 | CC(C)c1ccc(C2c3cc(NCc4ccccc4)ccc3OC2(C)C)cc1>>CC(C)c1ccc(C2c3cc(N)ccc3OC2(C)C)cc1 | C(C1=CC=CC=C1)NC=1C=CC2=C(C(C(O2)(C)C)C2=CC=C(C=C2)C(C)C)C1>>C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C=C(C=C2)N)(C)C | c1ccc(C[NH:12][c:11]2[cH:10][c:9]3[c:15]([cH:14][cH:13]2)[O:16][C:17]([CH3:18])([CH3:19])[CH:8]3[c:7]2[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:21][cH:20]2)cc1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[c:9]3[cH:10][c:11]([NH2:12])[cH:13][cH:14][c:15]3[O:16][C:17]2([CH3:18])[CH3:19])[cH:20][cH:21]1 | CC(C)c1ccc(C2c3cc(NCc4ccccc4)ccc3OC2(C)C)cc1 | CC(C)c1ccc(C2c3cc(N)ccc3OC2(C)C)cc1 | null | null | CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(C2COc3ccccc32)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 98 | [{"value": 98.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C=C(C=C2)N)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-3-(4-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 85, the title compound was synthesized in the same manner as in Reference Example 30. Yield 98%. Melting point: 109-110° C. (hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Ref... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | CCCCCC | null | null | CC(C)c1ccc(C2c3cc(NCc4ccccc4)ccc3OC2(C)C)cc1>CCCCCC>CC(C)c1ccc(C2c3cc(N)ccc3OC2(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aad60748f30349b1b484680a1b3b7c84 | CC(=Cc1ccc(C(C)C)cc1)CBr.Cc1ccc(O)cc1>>CC(=Cc1ccc(C(C)C)cc1)COc1ccc(C)cc1 | O.BrCC(=CC1=CC=C(C=C1)C(C)C)C.C1=CC(=CC=C1O)C.[H-].[Na+]>>C(C)(C)C1=CC=C(C=C1)C=C(COC1=CC=C(C=C1)C)C | Br[CH2:13][C:2]([CH3:1])=[CH:3][c:4]1[cH:5][cH:6][c:7]([CH:8]([CH3:9])[CH3:10])[cH:11][cH:12]1.[OH:14][c:15]1[cH:16][cH:17][c:18]([CH3:19])[cH:20][cH:21]1>>[CH3:1][C:2](=[CH:3][c:4]1[cH:5][cH:6][c:7]([CH:8]([CH3:9])[CH3:10])[cH:11][cH:12]1)[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]([CH3:19])[cH:20][cH:21]1 | CC(=Cc1ccc(C(C)C)cc1)CBr.Cc1ccc(O)cc1 | CC(=Cc1ccc(C(C)C)cc1)COc1ccc(C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | C(=Cc1ccccc1)COc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[C:4]-[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:3]-[C:2](=[C:4]-[c:5])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 91 | [{"value": 91.0, "product": "C(C)(C)C1=CC=C(C=C1)C=C(COC1=CC=C(C=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "C(C)(C)C1=CC=C(C=C1)C=C(COC1=CC=C(C=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of p-cresol (3.50 g, 32.3 mmol) in DMF (70 mL) was added sodium hydride (a 60% liquid paraffin dispersion, 1.42 g, 35.5 mmol) under nitrogen atmosphere at 0° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction solution was added 1-(3-bromo-2-methyl-1-propenyl)-4-isoprop... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | 0.5 | CC(=Cc1ccc(C(C)C)cc1)CBr.Cc1ccc(O)cc1>CN(C)C=O>CC(=Cc1ccc(C(C)C)cc1)COc1ccc(C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d38422b333b540758dabc5502807840a | CC(=Cc1ccc(C(C)C)cc1)COc1ccc(C)cc1>>C=C(C)C(c1ccc(C(C)C)cc1)c1cc(C)ccc1O | C(C)(C)C1=CC=C(C=C1)C=C(COC1=CC=C(C=C1)C)C>>C(C)(C)C1=CC=C(C=C1)C(C(=C)C)C1=C(C=CC(=C1)C)O | [CH2:1]([C:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[cH:12][cH:13]1)[O:21][c:20]1[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]1>>[CH2:1]=[C:2]([CH3:3])[CH:4]([c:5]1[cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[cH:12][cH:13]1)[c:14]1[cH:15][c:16]([CH3:17])[cH:18][cH:19][c:20]1[OH:21] | CC(=Cc1ccc(C(C)C)cc1)COc1ccc(C)cc1 | C=C(C)C(c1ccc(C(C)C)cc1)c1cc(C)ccc1O | null | null | CN(C1=CC=CC=C1)C.C(C)(C)OC(C)C | Miscellaneous | OtherReaction | b75155b152f2323e33b77ed6ec85548ee0adafb0a5b89b0b2df41caeacf0b82c | 39a337f27c7b73d892a2a429733dfdd8800f0f2eed92269e198b5632100ca547 | c1ccc(Cc2ccccc2)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9])=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[CH2;D1;+0:3])-[CH;D3;+0:10](-[c:11](:[c:12]):[c:13])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](-[OH;D1;+0:4]):[c:6] | 95 | [{"value": 95.0, "product": "C(C)(C)C1=CC=C(C=C1)C(C(=C)C)C1=C(C=CC(=C1)C)O", "details": "PERCENTYIELD", "is_desired": false}] | 215 | CELSIUS | 16 | HOUR | A solution of 1-isopropyl-4-(2-methyl-3-(4-methylphenoxy)propene-1-yl)benzene obtained in Reference Example 87 (8.2 g, 29.2 mmol) in N,N-dimethylaniline (50 mL) was stirred under argon atmosphere at 215° C. for 16 hours. After cooling, the reaction mixture was diluted with diisopropyl ether, washed with 5 N hydrochlori... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol.Vinyl | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | CN(C1=CC=CC=C1)C.C(C)(C)OC(C)C | 215 | 16 | CC(=Cc1ccc(C(C)C)cc1)COc1ccc(C)cc1>CN(C1=CC=CC=C1)C.C(C)(C)OC(C)C>C=C(C)C(c1ccc(C(C)C)cc1)c1cc(C)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-67ca99a570af446a9db2b4ad41adf7bc | Cc1cc2c(c(C)c1NCc1ccccc1)C(=O)C(C)(C)O2>>Cc1cc2c(c(C)c1NCc1ccccc1)C(O)C(C)(C)O2 | C(C1=CC=CC=C1)NC=1C(=CC2=C(C(C(O2)(C)C)=O)C1C)C.[BH4-].[Na+]>>C(C1=CC=CC=C1)NC=1C(=CC2=C(C(C(O2)(C)C)O)C1C)C | [CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])[C:19]([CH3:20])([CH3:21])[O:22]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[CH:17]([OH:18])[C:19]([CH3:20])([CH3:21])[O:22]2 | Cc1cc2c(c(C)c1NCc1ccccc1)C(=O)C(C)(C)O2 | Cc1cc2c(c(C)c1NCc1ccccc1)C(O)C(C)(C)O2 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 755c7bdda3ccaa9e2a097b82c386f43f2881f1d49e6c3707dce72c3ac00b51db | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(CNc2ccc3c(c2)CCO3)cc1 | [C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[#8:4]-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[#8:4]-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | null | [] | null | null | 2 | HOUR | To a solution of 5-(benzylamino)-2,2,4,6-tetramethyl-1-benzofuran-3(2H)-one obtained in Reference Example 51 (8.5 g, 28.8 mmol) in methanol (20 mL) was added sodium borohydride (2.18 g, 57.6 mmol) at room temperature, and the mixture was stirred for 2 hours. The reaction solution was concentrated under reduced pressure... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | null | CO | null | 2 | Cc1cc2c(c(C)c1NCc1ccccc1)C(=O)C(C)(C)O2>CO>Cc1cc2c(c(C)c1NCc1ccccc1)C(O)C(C)(C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7399efa988b74eafa43d6ae871129c0d | CC(C)c1ccc(C=O)cc1.CCOC(=O)C(C)P(=O)(OCC)OCC>>CCOC(=O)C(C)=Cc1ccc(C(C)C)cc1 | CCOC(=O)C(C)P(=O)(OCC)OCC.O.[H-].[Na+].C(C)(C)C1=CC=C(C=O)C=C1>>C(C)(C)C1=CC=C(C=C1)C=C(C(=O)OCC)C | O=[CH:8][c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1.CCOP(=O)(OCC)[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])=[CH:8][c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1 | CC(C)c1ccc(C=O)cc1.CCOC(=O)C(C)P(=O)(OCC)OCC | CCOC(=O)C(C)=Cc1ccc(C(C)C)cc1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccccc1 | C-C-O-P(=O)(-O-C-C)-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].O=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](-[C;D1;H3:2])=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 96 | [{"value": 96.0, "product": "C(C)(C)C1=CC=C(C=C1)C=C(C(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.0, "product": "C(C)(C)C1=CC=C(C=C1)C=C(C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a suspension of sodium hydride (a 60% liquid paraffin dispersion, 5.92 g, 148 mmol) in DMF (150 mL) was added triethyl 2-phosphonopropionate (35.0 g, 148 mmol) at 0° C., and the mixture was stirred at the same temperature for 10 minutes. To the reaction solution was added 4-isopropylbenzaldehyde (20.0 g, 135 mmol), ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1ccccc1 | HO- | CN(C)C=O | null | 0.166667 | CC(C)c1ccc(C=O)cc1.CCOC(=O)C(C)P(=O)(OCC)OCC>CN(C)C=O>CCOC(=O)C(C)=Cc1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-01e411290f4348ac86830b8e10f70f16 | CC(C)(C)[O-].O=Cc1ccc(Br)cc1>>CC(=Cc1ccc(Br)cc1)CO | O.BrC1=CC=C(C=O)C=C1.CC(C)([O-])C.[Na+]>>BrC1=CC=C(C=C1)C=C(CO)C | C[C:2]([O-])([CH3:1])[CH3:11].[CH:3]([c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1)=[O:12]>>[CH3:1][C:2](=[CH:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1)[CH2:11][OH:12] | CC(C)(C)[O-].O=Cc1ccc(Br)cc1 | CC(=Cc1ccc(Br)cc1)CO | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | f11de8ce6aae1931b2743d1c37dcfa7e7c31545d382a6d6f5c37348a82cd84f9 | 4f4da0c1ebb77155de3f9ccc4c0dc6683bc5c9f8cb0ed7c893695027b0c499da | c1ccccc1 | C-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[CH3;D1;+0:3])-[O-].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](-[CH2;D2;+0:3]-[OH;D1;+0:4])=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 88 | [{"value": 88.0, "product": "BrC1=CC=C(C=C1)C=C(CO)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of sodium tert-butoxide (10.6 g, 110 mmol) in DMF (60 mL) was added triethyl phosphonoacetate (26.2 g, 110 mmol) under argon atmosphere at −10° C. and the mixture was stirred at the same temperature for 1 hour. 4-bromobenzaldehyde (18.5 g, 100 mmol) was added to the solution at 10° C. or lower, and the mi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | HO- | CN(C)C=O | null | 1 | CC(C)(C)[O-].O=Cc1ccc(Br)cc1>CN(C)C=O>CC(=Cc1ccc(Br)cc1)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e20631283514e81b42c54b67862b580 | BrP(Br)Br.CC(=Cc1ccc(C(C)C)cc1)CO>>CC(=Cc1ccc(C(C)C)cc1)CBr | O.C(C)(C)C1=CC=C(C=C1)C=C(CO)C.P(Br)(Br)Br>>BrCC(=CC1=CC=C(C=C1)C(C)C)C | BrP(Br)[Br:14].O[CH2:13][C:2]([CH3:1])=[CH:3][c:4]1[cH:5][cH:6][c:7]([CH:8]([CH3:9])[CH3:10])[cH:11][cH:12]1>>[CH3:1][C:2](=[CH:3][c:4]1[cH:5][cH:6][c:7]([CH:8]([CH3:9])[CH3:10])[cH:11][cH:12]1)[CH2:13][Br:14] | BrP(Br)Br.CC(=Cc1ccc(C(C)C)cc1)CO | CC(=Cc1ccc(C(C)C)cc1)CBr | null | null | C(C)(C)OC(C)C | Functional Group Interconversion | PBr3 and alcohol to alkyl bromide | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3](-[C;D1;H3:4])=[C:5]-[c:6]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](-[C;D1;H3:4])=[C:5]-[c:6] | 91 | [{"value": 91.0, "product": "BrCC(=CC1=CC=C(C=C1)C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 3-(4-isopropylphenyl)-2-methyl-2-propen-1-ol synthesized in Reference Example 103 (6.30 g, 33.1 mmol) in isopropyl ether (50 mL) was added phosphorus tribromide (5.98 g, 22.1 mmol) with ice-cooling and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction solution ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HBr | C(C)(C)OC(C)C | null | 0.5 | BrP(Br)Br.CC(=Cc1ccc(C(C)C)cc1)CO>C(C)(C)OC(C)C>CC(=Cc1ccc(C(C)C)cc1)CBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc294752030e42309020e2ebf11e0a9f | BrBr.CC(=Cc1ccc(Br)cc1)CO>>CC(=Cc1ccc(Br)cc1)CBr | BrC1=CC=C(C=C1)C=C(CO)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.BrBr>>BrC1=CC=C(C=C1)C=C(CBr)C | Br[Br:12].O[CH2:11][C:2]([CH3:1])=[CH:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1>>[CH3:1][C:2](=[CH:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1)[CH2:11][Br:12] | BrBr.CC(=Cc1ccc(Br)cc1)CO | CC(=Cc1ccc(Br)cc1)CBr | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | Br-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3](-[C;D1;H3:4])=[C:5]-[c:6]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](-[C;D1;H3:4])=[C:5]-[c:6] | 98 | [{"value": 98.0, "product": "BrC1=CC=C(C=C1)C=C(CBr)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To an acetonitrile solution (180 mL) of triphenylphosphine (24.3 g, 92.7 mmol) was added dropwise bromine (4.78 mL, 185 mmol) at 0° C. and the mixture was stirred at the same temperature for 30 minutes. To the solution was added the acetonitrile solution (60 mL) of 3-(4-bromophenyl)-2-methyl-2-propen-1-ol obtained in R... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HBr | C(C)#N | null | 0.5 | BrBr.CC(=Cc1ccc(Br)cc1)CO>C(C)#N>CC(=Cc1ccc(Br)cc1)CBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc93ca00e0ac440ea16e69be383eabfa | CC(=Cc1ccc(C(C)C)cc1)CBr.Cc1cc(O)c(C)c(C)c1NC=O>>CC(=Cc1ccc(C(C)C)cc1)COc1cc(C)c(NC=O)c(C)c1C | O.OC1=C(C(=C(C(=C1)C)NC=O)C)C.[H-].[Na+].BrCC(=CC1=CC=C(C=C1)C(C)C)C>>C(C)(C)C1=CC=C(C=C1)C=C(COC1=C(C(=C(C(=C1)C)NC=O)C)C)C | Br[CH2:13][C:2]([CH3:1])=[CH:3][c:4]1[cH:5][cH:6][c:7]([CH:8]([CH3:9])[CH3:10])[cH:11][cH:12]1.[OH:14][c:15]1[cH:16][c:17]([CH3:18])[c:19]([NH:20][CH:21]=[O:22])[c:23]([CH3:24])[c:25]1[CH3:26]>>[CH3:1][C:2](=[CH:3][c:4]1[cH:5][cH:6][c:7]([CH:8]([CH3:9])[CH3:10])[cH:11][cH:12]1)[CH2:13][O:14][c:15]1[cH:16][c:17]([CH3:18... | CC(=Cc1ccc(C(C)C)cc1)CBr.Cc1cc(O)c(C)c(C)c1NC=O | CC(=Cc1ccc(C(C)C)cc1)COc1cc(C)c(NC=O)c(C)c1C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | C(=Cc1ccccc1)COc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[C:4]-[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:3]-[C:2](=[C:4]-[c:5])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 63 | [{"value": 63.0, "product": "C(C)(C)C1=CC=C(C=C1)C=C(COC1=C(C(=C(C(=C1)C)NC=O)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of N-(4-hydroxy-2,3,6-trimethylphenyl)formamide (3.00 g, 16.7 mmol) in DMF (30 mL) was added sodium hydride (a 60% liquid paraffin dispersion, 0.74 g, 18.4 mmol) under nitrogen atmosphere at 0° C., and the mixture was stirred at the same temperature for 10 minutes. To the reaction solution was added 1-(3-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | 0.166667 | CC(=Cc1ccc(C(C)C)cc1)CBr.Cc1cc(O)c(C)c(C)c1NC=O>CN(C)C=O>CC(=Cc1ccc(C(C)C)cc1)COc1cc(C)c(NC=O)c(C)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d581bba9f39d4e5893fa9a5b878182ff | COS(=O)(=O)OC.Cc1cc(O)c(C)c(C)c1NC=O>>COc1cc(C)c(NC=O)c(C)c1C | OC1=C(C(=C(C(=C1)C)NC=O)C)C.S(=O)(=O)(OC)OC>>COC1=C(C(=C(C(=C1)C)NC=O)C)C | COS(=O)(=O)O[CH3:1].[OH:2][c:3]1[cH:4][c:5]([CH3:6])[c:7]([NH:8][CH:9]=[O:10])[c:11]([CH3:12])[c:13]1[CH3:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[c:7]([NH:8][CH:9]=[O:10])[c:11]([CH3:12])[c:13]1[CH3:14] | COS(=O)(=O)OC.Cc1cc(O)c(C)c(C)c1NC=O | COc1cc(C)c(NC=O)c(C)c1C | null | null | [OH-].[K+].CO | Heteroatom Alkylation and Arylation | Methylation of OH with DMS | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccccc1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | N-(4-Hydroxy-2,3,6-trimethylphenyl)formamide (30.0 g, 167 mmol) was dissolved in a mixed solvent of 4 N potassium hydroxide aqueous solution (100 mL) and methanol (300 mL), and dimethyl sulfate (42.0 g, 334 mmol) was added to the solution at room temperature and the mixture was heated under reflux for 14 hours. After i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1 | HO- | [OH-].[K+].CO | null | null | COS(=O)(=O)OC.Cc1cc(O)c(C)c(C)c1NC=O>[OH-].[K+].CO>COc1cc(C)c(NC=O)c(C)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c37d4500c67b446e91009abab96e2a2c | BrBr.COc1cc(C)c(NC(=O)OC(C)(C)C)c(C)c1C>>COc1c(C)c(C)c(NC(=O)OC(C)(C)C)c(C)c1Br | BrBr.COC1=C(C(=C(C(=C1)C)NC(OC(C)(C)C)=O)C)C.O.C(C)(=O)[O-].[Na+]>>BrC=1C(=C(C(=C(C1OC)C)C)NC(OC(C)(C)C)=O)C | Br[Br:20].[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]([CH3:18])[cH:19]1>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]([CH3:18])[c:19]1[Br:20] | BrBr.COc1cc(C)c(NC(=O)OC(C)(C)C)c(C)c1C | COc1c(C)c(C)c(NC(=O)OC(C)(C)C)c(C)c1Br | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Br-[Br;H0;D1;+0:1].[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[C;D1;H3:7]):[c:8]>>[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6](-[C;D1;H3:7]):[c:8] | 91 | [{"value": 91.0, "product": "BrC=1C(=C(C(=C(C1OC)C)C)NC(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of tert-butyl 4-methoxy-2,3,6-trimethylphenylcarbamate synthesized in Reference Example 128 (12.7 g, 47.9 mmol) and sodium acetate (4.72 g, 57.5 mmol) in acetic acid (50 mL) was added bromine (8.42 g, 52.7 mmol) at room temperature and the mixture was stirred at the same temperature for 1 hour. Water (80 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)(=O)O | null | 1 | BrBr.COc1cc(C)c(NC(=O)OC(C)(C)C)c(C)c1C>C(C)(=O)O>COc1c(C)c(C)c(NC(=O)OC(C)(C)C)c(C)c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a05f66c400044a38de6e293bd21ea72 | COc1c(C)c(C)c(NC(=O)OC(C)(C)C)c(C)c1Br.Cc1ccc(C(=O)C(C)C)cc1>>Cc1ccc(C2c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1 | BrC=1C(=C(C(=C(C1OC)C)C)NC(OC(C)(C)C)=O)C.Br.C(CCC)[Li].CC(C(=O)C1=CC=C(C=C1)C)C.[OH-].[Na+].C1CCOC1>>CC1(OC2=C(C1C1=CC=C(C=C1)C)C(=C(C(=C2C)C)N)C)C | CC(C)(C)OC(=O)[NH:11][c:10]1[c:8]([CH3:9])[c:7](Br)[c:16]([O:17]C)[c:14]([CH3:15])[c:12]1[CH3:13].O=[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:22][cH:21]1)[CH:18]([CH3:19])[CH3:20]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[c:7]3[c:8]([CH3:9])[c:10]([NH2:11])[c:12]([CH3:13])[c:14]([CH3:15])[c:16]3[O:17][C:18]2([CH3:19])[CH... | COc1c(C)c(C)c(NC(=O)OC(C)(C)C)c(C)c1Br.Cc1ccc(C(=O)C(C)C)cc1 | Cc1ccc(C2c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 83a921042e81c7df82d28156d0ec8c578208dfaf866a836d1760d925ef450c4d | 8e3de543a4256d430df17aaec49274e2668ccfd8c14a580ba7df511ae08ad10e | c1ccc(C2COc3ccccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2](-[O;H0;D2;+0:3]-C):[c:4]:[c:5]:[c:6](-[NH;D2;+0:7]-C(=O)-O-C(-C)(-C)-C):[c:8]:1-[C;D1;H3:9].O=[C;H0;D3;+0:10](-[CH;D3;+0:11](-[C;D1;H3:12])-[C;D1;H3:13])-[c:14](:[c:15]):[c:16]>>[C;D1;H3:12]-[C;H0;D4;+0:11]1(-[C;D1;H3:13])-[O;H0;D2;+0:3]-[c:2]2:[c:4]:[c:5]:[c:6](-[NH2;D1;+0:7]):[c:8](-[C;D1;H3:... | 62 | [{"value": 62.0, "product": "CC1(OC2=C(C1C1=CC=C(C=C1)C)C(=C(C(=C2C)C)N)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of tert-butyl 3-bromo-4-methoxy-2,5,6-trimethylphenylcarbamate synthesized in Reference Example 129 (27.8 g, 80.8 mmol) in THF (150 mL) was added n-butyllithium (1.6 M, 110 mL, 176 mmol) hexane solution at −78° C. and the mixture was stirred at the same temperature for 20 minutes. 2-Methyl-1-(4-methylphen... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ketone.Ether.Ether.Boc | Ether.Primary amine | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HBr | O | null | 0.333333 | COc1c(C)c(C)c(NC(=O)OC(C)(C)C)c(C)c1Br.Cc1ccc(C(=O)C(C)C)cc1>O>Cc1ccc(C2c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89feb5e31fa848e9b03e5b269edaf633 | CC(C)(Br)C(=O)c1ccc(Br)cc1.Cc1cccc(O)c1C>>Cc1ccc(C(=O)C(C)(C)Oc2cccc(C)c2C)cc1 | O.CC1=C(C=CC=C1C)O.C([O-])([O-])=O.[K+].[K+].BrC(C(=O)C1=CC=C(C=C1)Br)(C)C>>CC1=C(OC(C(=O)C2=CC=C(C=C2)C)(C)C)C=CC=C1C | Br[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[C:8](Br)([CH3:9])[CH3:10])[cH:20][cH:21]1.[OH:11][c:12]1[cH:13][cH:14][cH:15][c:16]([CH3:17])[c:18]1[CH3:19]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[C:8]([CH3:9])([CH3:10])[O:11][c:12]2[cH:13][cH:14][cH:15][c:16]([CH3:17])[c:18]2[CH3:19])[cH:20][cH:21]1 | CC(C)(Br)C(=O)c1ccc(Br)cc1.Cc1cccc(O)c1C | Cc1ccc(C(=O)C(C)(C)Oc2cccc(C)c2C)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 2b2b214b3256905650efd4b30d39719df81dcdc20143eeaaad86e37ab684292b | 9d666779d213eb35efd66c7c5f2a93415132bdf22366a901eff054e84b5f3b5d | O=C(COc1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C:5](=[O;D1;H0:6])-[C;H0;D4;+0:7](-Br)(-[C;D1;H3:8])-[C;D1;H3:9]):[c:10]:[c:11]:1.[OH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H3:8]-[C;H0;D4;+0:7](-[C;D1;H3:9])(-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15])-[C:5](=[O;D1;H0:6])-[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;D1;H3:16]):[c:11]:[c:... | null | [] | 35 | CELSIUS | 24 | HOUR | To a mixture of 2,3-dimethylphenol (12.2 g, 100 mmol) and potassium carbonate (27.4 g, 200 mmol) in dimethylsulfoxide (138 mL) was added 2-bromo-1-(4-bromophenyl)-2-methylpropane-1-one (42.2 g, 175 mmol) at room temperature, and the mixture was warmed to 35° C. The mixture was stirred at the same temperature for 24 hou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary halide.Ketone.Aromatic alcohol | Ketone.Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | CS(=O)C | 35 | 24 | CC(C)(Br)C(=O)c1ccc(Br)cc1.Cc1cccc(O)c1C>CS(=O)C>Cc1ccc(C(=O)C(C)(C)Oc2cccc(C)c2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b9d43123ec34e4f93e9ad96c6fa974a | Cc1ccc(C(O)C(C)(C)Oc2cccc(C)c2C)cc1>>Cc1ccc(C2c3ccc(C)c(C)c3OC2(C)C)cc1 | C(O)([O-])=O.[Na+].CC1=C(OC(C(O)C2=CC=C(C=C2)C)(C)C)C=CC=C1C.FC(S(=O)(=O)[O-])(F)F>>CC1(OC2=C(C1C1=CC=C(C=C1)C)C=CC(=C2C)C)C | O[CH:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]1)[C:16]([O:15][c:14]1[cH:7][cH:8][cH:9][c:10]([CH3:11])[c:12]1[CH3:13])([CH3:17])[CH3:18]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[c:7]3[cH:8][cH:9][c:10]([CH3:11])[c:12]([CH3:13])[c:14]3[O:15][C:16]2([CH3:17])[CH3:18])[cH:19][cH:20]1 | Cc1ccc(C(O)C(C)(C)Oc2cccc(C)c2C)cc1 | Cc1ccc(C2c3ccc(C)c(C)c3OC2(C)C)cc1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 65fcbc560307aa9109a332daa2c2899a0eac338a1489b81f286ef8fc2d062531 | f8118e7f3e1d7109575c0c77239dee8da98ec71a2b23460bcda2084274bdf7e7 | c1ccc(C2COc3ccccc32)cc1 | O-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:8]-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[C;D1;H3:6]-[C:5]1(-[C;D1;H3:7])-[#8:8]-[c:9](:[c:10]):[c;H0;D3;+0:11](:[c:12]:[c:13])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 58 | [{"value": 58.0, "product": "CC1(OC2=C(C1C1=CC=C(C=C1)C)C=CC(=C2C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | To a solution of 2-(2,3-dimethylphenoxy)-2-methyl-1-(4-methylphenyl)propane-1-ol synthesized in Reference Example 135 (17.0 g, 60 mmol) in toluene (200 mL) was added trifluoromethanesulfonate (0.53 mL, 6 mmol) at 0° C., and the mixture was warmed to 50° C. The mixture was stirred at the same temperature for 30 minutes ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C1(=CC=CC=C1)C | 50 | 0.5 | Cc1ccc(C(O)C(C)(C)Oc2cccc(C)c2C)cc1>C1(=CC=CC=C1)C>Cc1ccc(C2c3ccc(C)c(C)c3OC2(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0458a279ef14249bba2f2f0c0239953 | Cc1ccc(C2c3cc(NCc4ccccc4)c(C)c(C)c3OC2(C)C)cc1>>Cc1ccc(C2c3cc(N)c(C)c(C)c3OC2(C)C)cc1 | Cl.C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(C(O2)(C)C)C2=CC=C(C=C2)C)C1)C)C>>CC1(OC2=C(C1C1=CC=C(C=C1)C)C=C(C(=C2C)C)N)C | c1ccc(C[NH:10][c:9]2[cH:8][c:7]3[c:15]([c:13]([CH3:14])[c:11]2[CH3:12])[O:16][C:17]([CH3:18])([CH3:19])[CH:6]3[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]2)cc1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[c:7]3[cH:8][c:9]([NH2:10])[c:11]([CH3:12])[c:13]([CH3:14])[c:15]3[O:16][C:17]2([CH3:18])[CH3:19])[cH:20][cH:21]1 | Cc1ccc(C2c3cc(NCc4ccccc4)c(C)c(C)c3OC2(C)C)cc1 | Cc1ccc(C2c3cc(N)c(C)c(C)c3OC2(C)C)cc1 | null | [C].[Pd] | C(C)O | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(C2COc3ccccc32)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 88 | [{"value": 88.0, "product": "CC1(OC2=C(C1C1=CC=C(C=C1)C)C=C(C(=C2C)C)N)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of N-benzyl-2,2,6,7-tetramethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 138 (6.60 g, 17.8 mmol) in ethanol (70 mL) was added 12 N hydrochloric acid (0.1 mL) and 10%-palladium carbon (hydrous 50%, 0.33 g), and the mixture was stirred under hydrogen condition of 5 a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | [C].[Pd].C(C)O | null | 2 | Cc1ccc(C2c3cc(NCc4ccccc4)c(C)c(C)c3OC2(C)C)cc1>[C].[Pd].C(C)O>Cc1ccc(C2c3cc(N)c(C)c(C)c3OC2(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-20f2e46b71124d74bb5bae7fedc8f625 | Cc1cc2c(c(C)c1N)C(c1ccc(C(C)C)cc1)CO2>>Cc1cc2c(c(C)c1N)[C@@H](c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2)C)N)C>>C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2)C)N)C | [CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH2:9])[CH:10]([c:11]1[cH:12][cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]1)[CH2:20][O:21]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH2:9])[C@@H:10]([c:11]1[cH:12][cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]1)[CH2:20][O:21]2 | Cc1cc2c(c(C)c1N)C(c1ccc(C(C)C)cc1)CO2 | Cc1cc2c(c(C)c1N)[C@@H](c1ccc(C(C)C)cc1)CO2 | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc([C@H]2COc3ccccc32)cc1 | null | 34 | [{"value": 34.0, "product": "C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2)C)N)C", "details": "PERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A suspension of 3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 32 (22.5 g, 80 mmol) and (2S, 3S)-(4′-methyl)-tartranilic acid (19.14 g, 80 mmol) in ethanol (480 mL) was heated at 85° C. for dissolution. The solution was cooled to 0° C. for 2 hours, and the precipitated... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | null | C(C)O | 85 | null | Cc1cc2c(c(C)c1N)C(c1ccc(C(C)C)cc1)CO2>C(C)O>Cc1cc2c(c(C)c1N)[C@@H](c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bdfdb7fc84a14927a0d813fd6345543c | CC(C)c1ccccc1.O=C(Br)CBr>>CC(C)c1ccc(C(=O)CBr)cc1 | C1(=CC=CC=C1)C(C)C.[Cl-].[Al+3].[Cl-].[Cl-].BrCC(=O)Br>>BrCC(=O)C1=CC=C(C=C1)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:12][cH:13]1.Br[C:8](=[O:9])[CH2:10][Br:11]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][Br:11])[cH:12][cH:13]1 | CC(C)c1ccccc1.O=C(Br)CBr | CC(C)c1ccc(C(=O)CBr)cc1 | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | 2 | HOUR | To a solution of cumene (27.8 mL, 200 mmol) and aluminum chloride (32.0 g, 240 mmol) in dichloromethane (300 mL) was added bromoacetylbromide (19.1 mL, 220 mmol) at −10° C., and the mixture was stirred at the same temperature for 2 hours. The reaction solution was poured into ice-cold water, and an organic layer was se... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | ClCCl | null | 2 | CC(C)c1ccccc1.O=C(Br)CBr>ClCCl>CC(C)c1ccc(C(=O)CBr)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0766e6e31bb0458ba9c4188e7527571d | COc1ccc(CCC(=O)O)cc1.Cc1ccc(C2c3cc(N)c(C)c(C)c3OC2(C)C)cc1>>COc1ccc(CCC(=O)Nc2cc3c(c(C)c2C)OC(C)(C)C3c2ccc(C)cc2)cc1 | CC1(OC2=C(C1C1=CC=C(C=C1)C)C=C(C(=C2C)C)N)C.COC1=CC=C(C=C1)CCC(=O)O>>COC1=CC=C(C=C1)CCC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)C2=CC=C(C=C2)C)C1)C)C | O[C:9]([CH2:8][CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33][cH:32]1)=[O:10].[NH2:11][c:12]1[cH:13][c:14]2[c:15]([c:16]([CH3:17])[c:18]1[CH3:19])[O:20][C:21]([CH3:22])([CH3:23])[CH:24]2[c:25]1[cH:26][cH:27][c:28]([CH3:29])[cH:30][cH:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][C:9](=[O:10])[NH:11][c:12... | COc1ccc(CCC(=O)O)cc1.Cc1ccc(C2c3cc(N)c(C)c(C)c3OC2(C)C)cc1 | COc1ccc(CCC(=O)Nc2cc3c(c(C)c2C)OC(C)(C)C3c2ccc(C)cc2)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1ccccc1)Nc1ccc2c(c1)C(c1ccccc1)CO2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 64 | [{"value": 64.0, "product": "COC1=CC=C(C=C1)CCC(=O)NC=1C(=C(C2=C(C(C(O2)(C)C)C2=CC=C(C=C2)C)C1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,2,6,7-tetramethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine obtained Reference Example 139 and 3-(4-methoxyphenyl)propionic acid, the title compound was obtained in the same manner as in Reference Example 359.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HO- | null | null | null | COc1ccc(CCC(=O)O)cc1.Cc1ccc(C2c3cc(N)c(C)c(C)c3OC2(C)C)cc1>>COc1ccc(CCC(=O)Nc2cc3c(c(C)c2C)OC(C)(C)C3c2ccc(C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a8ec02a46067491c9fcf32a61bc6e041 | CC(C)c1ccc(Br)cc1.Cc1cc(C)c(C=O)c(O)c1>>Cc1cc(C)c(C(O)c2ccc(C(C)C)cc2)c(O)c1 | OC1=C(C=O)C(=CC(=C1)C)C.BrC1=CC=C(C=C1)C(C)C.C(CCC)[Li].CCCCCC>>OC(C1=C(C=C(C=C1C)C)O)C1=CC=C(C=C1)C(C)C | Br[c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1.[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH:7]=[O:8])[c:18]([OH:19])[cH:20]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH:7]([OH:8])[c:9]2[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]2)[c:18]([OH:19])[cH:20]1 | CC(C)c1ccc(Br)cc1.Cc1cc(C)c(C=O)c(O)c1 | Cc1cc(C)c(C(O)c2ccc(C(C)C)cc2)c(O)c1 | null | null | O.C1CCOC1 | C-C Coupling | Grignard_alcohol | 0c8bc0f755f4d9a2cfce93ae43a9a9a531fa8ad86ff120aed0a18ba03c84e4d7 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(Cc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 91 | [{"value": 91.0, "product": "OC(C1=C(C=C(C=C1C)C)O)C1=CC=C(C=C1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 1-bromo-4-isopropylbenzene (3.32 g, 16.7 mmol) in THF (30 mL) was added dropwise n-butyllithium (a 1.59 M hexane solution, 9.2 mL, 14.7 mmol) under argon atmosphere at −78° C. The reaction solution was stirred for 30 minutes, a solution of 2-hydroxy-4,6-dimethylbenzaldehyde obtained in Reference Exampl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | O.C1CCOC1 | null | 0.5 | CC(C)c1ccc(Br)cc1.Cc1cc(C)c(C=O)c(O)c1>O.C1CCOC1>Cc1cc(C)c(C(O)c2ccc(C(C)C)cc2)c(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3ee0d8a924914801b3fbf562509f919b | Cc1cc(C)cc(O)c1.O=C1CCC(=O)N1Br>>Cc1cc(C)c(Br)c(O)c1 | CC=1C=C(C=C(C1)C)O.BrN1C(CCC1=O)=O>>BrC1=C(C=C(C=C1C)C)O | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:8]([OH:9])[cH:10]1.O=C1CCC(=O)N1[Br:7]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([Br:7])[c:8]([OH:9])[cH:10]1 | Cc1cc(C)cc(O)c1.O=C1CCC(=O)N1Br | Cc1cc(C)c(Br)c(O)c1 | null | null | C(=S)=S | Functional Group Interconversion | Bromination | 48c1dcf50945076da40bbd7976060ec1ea74b3478ef8c25d67664232b218095c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C;D1;H3:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[O;D1;H1:7]):[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:3](-[C;D1;H3:2]):[c:4]):[c:6](-[O;D1;H1:7]):[c:8] | 66 | [{"value": 66.0, "product": "BrC1=C(C=C(C=C1C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.9, "product": "BrC1=C(C=C(C=C1C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3,5-dimethylphenol (15.0 g, 123 mmol) in carbon disulfide (330 mL) was slowly added N-bromosuccinimide (21.9 g, 123 mmol) in several batches with ice-cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and the precipitated crystals ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccccc1.C1CCNC1 | c1ccccc1 | c1ccccc1 | HO- | C(=S)=S | null | 1 | Cc1cc(C)cc(O)c1.O=C1CCC(=O)N1Br>C(=S)=S>Cc1cc(C)c(Br)c(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba9b7965008946d2ab79928044140f6f | CCOC(=O)CBr.Cc1cc(C)c(C)c(O)c1>>CCOC(=O)COc1cc(C)cc(C)c1C | CC1=C(C=C(C=C1C)C)O.BrCC(=O)OCC>>CC1=C(OCC(=O)OCC)C=C(C=C1C)C | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[cH:9][c:10]([CH3:11])[cH:12][c:13]([CH3:14])[c:15]1[CH3:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][c:10]([CH3:11])[cH:12][c:13]([CH3:14])[c:15]1[CH3:16] | CCOC(=O)CBr.Cc1cc(C)c(C)c(O)c1 | CCOC(=O)COc1cc(C)cc(C)c1C | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | Using 2,3,5-trimethylphenol and ethyl bromoacetate, the title compound was synthesized in the same manner as in Reference Example 153. Yield: quantitative. Oily matter.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | null | null | null | CCOC(=O)CBr.Cc1cc(C)c(C)c(O)c1>>CCOC(=O)COc1cc(C)cc(C)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72b487fe63864ee6a023f5c38c9ffc86 | CCOC(=O)C(C)(C)Oc1cc(C)cc(C)c1Cc1ccc(C(C)C)cc1>>Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OC(C)(C)C(=O)O)c1 | C(C)(C)C1=CC=C(CC2=C(OC(C(=O)OCC)(C)C)C=C(C=C2C)C)C=C1.[OH-].[Na+].C1CCOC1.Cl>>C(C)(C)C1=CC=C(CC2=C(OC(C(=O)O)(C)C)C=C(C=C2C)C)C=C1 | CC[O:24][C:22]([C:19]([O:18][c:17]1[c:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]2)[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:25]1)([CH3:20])[CH3:21])=[O:23]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]2)[c:17]([O:18][C:19]... | CCOC(=O)C(C)(C)Oc1cc(C)cc(C)c1Cc1ccc(C(C)C)cc1 | Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OC(C)(C)C(=O)O)c1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cc2ccccc2)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] | 91 | [{"value": 91.0, "product": "C(C)(C)C1=CC=C(CC2=C(OC(C(=O)O)(C)C)C=C(C=C2C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixed solution of ethyl 2-(2-(4-isopropylbenzyl)-3,5-dimethylphenoxy)-2-methylpropanoate obtained in Reference Example 153 (6.65 g, 18.1 mmol) and a 8 N aqueous sodium hydroxide solution (4.5 mL) in methanol (40 mL)-THF (20 mL) was stirred at room temperature for 16 hours. The reaction solution was acidified with hyd... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | CO | null | null | CCOC(=O)C(C)(C)Oc1cc(C)cc(C)c1Cc1ccc(C(C)C)cc1>CO>Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OC(C)(C)C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-76f55b6ab6db4b9986f1d9db704a757d | CCOC(=O)COc1cc(C)cc(C)c1Cc1ccc(C(C)C)cc1>>Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OCC(=O)O)c1 | C(C)(C)C1=CC=C(CC2=C(OCC(=O)OCC)C=C(C=C2C)C)C=C1>>C(C)(C)C1=CC=C(CC2=C(OCC(=O)O)C=C(C=C2C)C)C=C1 | CC[O:22][C:20]([CH2:19][O:18][c:17]1[c:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]2)[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:23]1)=[O:21]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]2)[c:17]([O:18][CH2:19][C:20](=[O:21])[... | CCOC(=O)COc1cc(C)cc(C)c1Cc1ccc(C(C)C)cc1 | Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OCC(=O)O)c1 | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cc2ccccc2)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] | 75 | [{"value": 75.0, "product": "C(C)(C)C1=CC=C(CC2=C(OCC(=O)O)C=C(C=C2C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using ethyl (2-(4-isopropylbenzyl)-3,5-dimethylphenoxy)acetate obtained in Reference Example 154, the title compound was synthesized in the same manner as in Reference Example 156. Yield 75%. Melting point: 104-105° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Referen... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | CCOC(=O)COc1cc(C)cc(C)c1Cc1ccc(C(C)C)cc1>C(C)(=O)OCC.CCCCCC>Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OCC(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-841553179ead41ae92fb9726a38fef87 | CC(=O)CCl.Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(O)c1>>CC(=O)COc1cc(C)cc(C)c1Cc1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(CC2=C(C=C(C=C2C)C)O)C=C1.[I-].[K+].C([O-])([O-])=O.[K+].[K+].ClCC(C)=O>>C(C)(C)C1=CC=C(CC2=C(OCC(=O)C)C=C(C=C2C)C)C=C1 | Cl[CH2:4][C:2]([CH3:1])=[O:3].[OH:5][c:6]1[cH:7][c:8]([CH3:9])[cH:10][c:11]([CH3:12])[c:13]1[CH2:14][c:15]1[cH:16][cH:17][c:18]([CH:19]([CH3:20])[CH3:21])[cH:22][cH:23]1>>[CH3:1][C:2](=[O:3])[CH2:4][O:5][c:6]1[cH:7][c:8]([CH3:9])[cH:10][c:11]([CH3:12])[c:13]1[CH2:14][c:15]1[cH:16][cH:17][c:18]([CH:19]([CH3:20])[CH3:21]... | CC(=O)CCl.Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(O)c1 | CC(=O)COc1cc(C)cc(C)c1Cc1ccc(C(C)C)cc1 | null | null | O.CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | c1ccc(Cc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 73 | [{"value": 73.0, "product": "C(C)(C)C1=CC=C(CC2=C(OCC(=O)C)C=C(C=C2C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixed solution of 2-(4-isopropylbenzyl)-3,5-dimethylphenol obtained in Reference Example 148 (1.0 g, 3.93 mmol), potassium carbonate (1.30 g, 9.44 mmol), chloroacetone (436 mg, 4.72 mmol) and potassium iodide (100 mg) in acetone (15 mL) was heated under reflux for 16 hours. Water was added to the reaction solution, w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1ccccc1.c1ccccc1 | HCl | O.CC(=O)C | null | null | CC(=O)CCl.Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(O)c1>O.CC(=O)C>CC(=O)COc1cc(C)cc(C)c1Cc1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-76328dece4224a42ac6d78dfe615c46b | Cc1cc(C)c(C)c(O)c1.O=C(CBr)c1cccc(Br)c1>>Cc1cc(C)c(C)c(OCC(=O)c2cccc(Br)c2)c1 | CC1=C(C=C(C=C1C)C)O.BrCC(=O)C1=CC(=CC=C1)Br>>BrC=1C=C(C=CC1)C(COC1=C(C(=CC(=C1)C)C)C)=O | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH3:7])[c:8]([OH:9])[cH:20]1.Br[CH2:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][c:17]([Br:18])[cH:19]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH3:7])[c:8]([O:9][CH2:10][C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]([Br:18])[cH:19]2)[cH:20]1 | Cc1cc(C)c(C)c(O)c1.O=C(CBr)c1cccc(Br)c1 | Cc1cc(C)c(C)c(OCC(=O)c2cccc(Br)c2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | O=C(COc1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 52 | [{"value": 52.0, "product": "BrC=1C=C(C=CC1)C(COC1=C(C(=CC(=C1)C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,3,5-trimethylphenol and 2-bromo-1-(3-bromophenyl)ethanone, the title compound was synthesized in the same manner as in Reference Example 159. Yield 52%. Oily matter.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1ccccc1.c1ccccc1 | HBr | null | null | null | Cc1cc(C)c(C)c(O)c1.O=C(CBr)c1cccc(Br)c1>>Cc1cc(C)c(C)c(OCC(=O)c2cccc(Br)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-52a2b141826c4269b5abfd8e957dd276 | COc1cccc(C(=O)CBr)c1.Cc1cc(C)c(C)c(O)c1>>COc1cccc(C(=O)COc2cc(C)cc(C)c2C)c1 | CC1=C(C=C(C=C1C)C)O.BrCC(=O)C1=CC(=CC=C1)OC>>COC=1C=C(C=CC1)C(COC1=C(C(=CC(=C1)C)C)C)=O | Br[CH2:10][C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21]1)=[O:9].[OH:11][c:12]1[cH:13][c:14]([CH3:15])[cH:16][c:17]([CH3:18])[c:19]1[CH3:20]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][O:11][c:12]2[cH:13][c:14]([CH3:15])[cH:16][c:17]([CH3:18])[c:19]2[CH3:20])[cH:21]1 | COc1cccc(C(=O)CBr)c1.Cc1cc(C)c(C)c(O)c1 | COc1cccc(C(=O)COc2cc(C)cc(C)c2C)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | O=C(COc1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 88 | [{"value": 88.0, "product": "COC=1C=C(C=CC1)C(COC1=C(C(=CC(=C1)C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,3,5-trimethylphenol and 2-bromo-1-(3-methoxyphenyl)ethanone, the title compound was synthesized in the same manner as in Reference Example 159. Yield 88%. Oily matter.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1ccccc1.c1ccccc1 | HBr | null | null | null | COc1cccc(C(=O)CBr)c1.Cc1cc(C)c(C)c(O)c1>>COc1cccc(C(=O)COc2cc(C)cc(C)c2C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a8f8409b65894cb8876433e12a2fb0d2 | Cc1cc(C)c(C)c(O)c1.Cc1ccc(C(=O)CBr)cc1>>Cc1ccc(C(=O)COc2cc(C)cc(C)c2C)cc1 | CC1=C(C=C(C=C1C)C)O.BrCC(=O)C1=CC=C(C=C1)C>>CC1=CC=C(C=C1)C(COC1=C(C(=CC(=C1)C)C)C)=O | [OH:9][c:10]1[cH:11][c:12]([CH3:13])[cH:14][c:15]([CH3:16])[c:17]1[CH3:18].Br[CH2:8][C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]1)=[O:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[CH2:8][O:9][c:10]2[cH:11][c:12]([CH3:13])[cH:14][c:15]([CH3:16])[c:17]2[CH3:18])[cH:19][cH:20]1 | Cc1cc(C)c(C)c(O)c1.Cc1ccc(C(=O)CBr)cc1 | Cc1ccc(C(=O)COc2cc(C)cc(C)c2C)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | O=C(COc1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 75 | [{"value": 75.0, "product": "CC1=CC=C(C=C1)C(COC1=C(C(=CC(=C1)C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,3,5-trimethylphenol and 2-bromo-1-(4-methylphenyl)ethanone, the title compound was synthesized in the same manner as in Reference Example 159. Yield 75%. Melting point: 94-95° C. (methanol).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CO | null | null | Cc1cc(C)c(C)c(O)c1.Cc1ccc(C(=O)CBr)cc1>CO>Cc1ccc(C(=O)COc2cc(C)cc(C)c2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ffa3335c06624450a23b11b09c0ba6bf | CC(C)c1ccccc1.O=C(Br)CBr>>CC(C)c1ccc(C(=O)CBr)cc1 | C1(=CC=CC=C1)C(C)C.[Cl-].[Al+3].[Cl-].[Cl-].BrCC(=O)Br>>BrCC(=O)C1=CC=C(C=C1)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:12][cH:13]1.Br[C:8](=[O:9])[CH2:10][Br:11]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][Br:11])[cH:12][cH:13]1 | CC(C)c1ccccc1.O=C(Br)CBr | CC(C)c1ccc(C(=O)CBr)cc1 | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | 99.5 | [{"value": 99.0, "product": "BrCC(=O)C1=CC=C(C=C1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.5, "product": "BrCC(=O)C1=CC=C(C=C1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | null | null | To a solution of cumene (42 g, 350 mmol) and aluminum chloride (56.0 g, 420 mmol) in dichloromethane (500 mL) was added bromoacetylbromide (33.5 mL, 385 mmol) at −40° C. for 40 minutes, and the mixture was stirred until it was warmed to −10° C. for 2 hours. The reaction solution was poured into ice-cold water to separa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | ClCCl | -10 | null | CC(C)c1ccccc1.O=C(Br)CBr>ClCCl>CC(C)c1ccc(C(=O)CBr)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf23ff1a360c478e808d10ef0f6751b0 | CC(C)c1ccc(C(=O)CBr)cc1.Cc1cc(O)c(C)c(C)c1Br>>Cc1cc(OCC(=O)c2ccc(C(C)C)cc2)c(C)c(C)c1Br | CC1=C(C=C(C=C1C)C)O.BrC1=C(C(=C(C=C1C)O)C)C.BrCC(=O)C1=CC=C(C=C1)C(C)C>>BrC1=C(C(=C(OCC(=O)C2=CC=C(C=C2)C(C)C)C=C1C)C)C | Br[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1.[CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:18]([CH3:19])[c:20]([CH3:21])[c:22]1[Br:23]>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]2)[c:18]([CH3:19])[c:20]([CH3:21... | CC(C)c1ccc(C(=O)CBr)cc1.Cc1cc(O)c(C)c(C)c1Br | Cc1cc(OCC(=O)c2ccc(C(C)C)cc2)c(C)c(C)c1Br | null | null | C(C)(=O)OCC.CCCCCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | O=C(COc1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 51 | [{"value": 51.0, "product": "BrC1=C(C(=C(OCC(=O)C2=CC=C(C=C2)C(C)C)C=C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,3,5-trimethylphenol, 4-bromo-2,3,5-trimethylphenol was synthesized in the same manner as in Reference Example 23. Using this compound and 2-bromo-1-(4-isopropylphenyl)ethanone obtained in Reference Example 164, the title compound was synthesized in the same manner as in Reference Example 159. Yield 51%. Melting... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1ccccc1.c1ccccc1 | HBr | C(C)(=O)OCC.CCCCCC | null | null | CC(C)c1ccc(C(=O)CBr)cc1.Cc1cc(O)c(C)c(C)c1Br>C(C)(=O)OCC.CCCCCC>Cc1cc(OCC(=O)c2ccc(C(C)C)cc2)c(C)c(C)c1Br |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.