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-418a8bb1d9cd4d4094b40707213f97e4 | CN1CCN(c2ccc(Nc3ncc4c(n3)N(C)C(=O)NC4)cc2)CC1>>CN1CCN(c2ccc(Nc3ncc4cnc(=O)n(C)c4n3)cc2)CC1 | CN1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O.FC(C(=O)O)(F)F.CC(C)([O-])C.[K+]>>CN1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]4[c:21]([n:22]3)[N:19]([CH3:20])[C:17](=[O:18])[NH:16][CH2:15]4)[cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]4[cH:15][n:16][c:17](=[O:18])[n:19]([CH3:... | CN1CCN(c2ccc(Nc3ncc4c(n3)N(C)C(=O)NC4)cc2)CC1 | CN1CCN(c2ccc(Nc3ncc4cnc(=O)n(C)c4n3)cc2)CC1 | null | null | O1CCCC1 | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccc(N4CCNCC4)cc3)nc2[nH]1 | [C;D1;H3:1]-[N;H0;D3;+0:2]1-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[CH2;D2;+0:6]-[c:7]2:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2-1>>[C;D1;H3:1]-[n;H0;D3;+0:2]1:[c:12]2:[#7;a:11]:[c:10]:[#7;a:9]:[c:8]:[c:7]:2:[cH;D2;+0:6]:[n;H0;D2;+0:5]:[c;H0;D3;+0:3]:1=[O;D1;H0:4] | 62.6 | [{"value": 61.0, "product": "CN1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.6, "product": "CN1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Prepared from 250 mg (0.50 mmol) of 1-methyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, trifluoroacetic acid and 336 mg (2.99 mmol) of potassium tert-butoxide in 12 mL of tetrahydrofuran. The reaction mixture is stirred for 48 hours. After the workup, the semi-solid is tri... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2cncnc2n1 | null | O1CCCC1 | null | 48 | CN1CCN(c2ccc(Nc3ncc4c(n3)N(C)C(=O)NC4)cc2)CC1>O1CCCC1>CN1CCN(c2ccc(Nc3ncc4cnc(=O)n(C)c4n3)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3aa7af4bf0824f759dd2992775b1e50f | CN1C(=O)NCc2cnc(Nc3ccc(N4CCC(N(C)C)CC4)cc3)nc21>>CN(C)C1CCN(c2ccc(Nc3ncc4cnc(=O)n(C)c4n3)cc2)CC1 | CN(C1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(NC2)=O)C)C.FC(C(=O)O)(F)F.CC(C)([O-])C.[K+]>>CN(C1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(N=C2)=O)C)C | [CH3:1][N:2]([CH3:3])[CH:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH:12][c:13]3[n:14][cH:15][c:16]4[c:23]([n:24]3)[N:21]([CH3:22])[C:19](=[O:20])[NH:18][CH2:17]4)[cH:25][cH:26]2)[CH2:27][CH2:28]1>>[CH3:1][N:2]([CH3:3])[CH:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH:12][c:13]3[n:14][cH:15][c:16]4[cH:17... | CN1C(=O)NCc2cnc(Nc3ccc(N4CCC(N(C)C)CC4)cc3)nc21 | CN(C)C1CCN(c2ccc(Nc3ncc4cnc(=O)n(C)c4n3)cc2)CC1 | null | null | O1CCCC1 | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccc(N4CCCCC4)cc3)nc2[nH]1 | [C;D1;H3:1]-[N;H0;D3;+0:2]1-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[CH2;D2;+0:6]-[c:7]2:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2-1>>[C;D1;H3:1]-[n;H0;D3;+0:2]1:[c:12]2:[#7;a:11]:[c:10]:[#7;a:9]:[c:8]:[c:7]:2:[cH;D2;+0:6]:[n;H0;D2;+0:5]:[c;H0;D3;+0:3]:1=[O;D1;H0:4] | 64.9 | [{"value": 60.0, "product": "CN(C1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(N=C2)=O)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.9, "product": "CN(C1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(N=C2)=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | DAY | Prepared from 170 mg (0.26 mmol) of 7-{4-[4-(dimethylamino)piperidin-1-yl]phenylamino}-1-methyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, trifluoroacetic acid and 233 mg (2.07 mmol) of potassium tert-butoxide in 20 mL of tetrahydrofuran. The reaction mixture is stirred for 6 days, and the workup is done as descri... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | C1CC[NH]CC1.c1ccccc1.c1ncc2cncnc2n1 | null | O1CCCC1 | null | 144 | CN1C(=O)NCc2cnc(Nc3ccc(N4CCC(N(C)C)CC4)cc3)nc21>O1CCCC1>CN(C)C1CCN(c2ccc(Nc3ncc4cnc(=O)n(C)c4n3)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f136ffd4cec4641934ba27aaa4c4d0d | CN1C(=O)NCc2cnc(Nc3ccc(-n4cccn4)cc3)nc21>>Cn1c(=O)ncc2cnc(Nc3ccc(-n4cccn4)cc3)nc21 | CN1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2N=CC=C2)=O.FC(C(=O)O)(F)F.CC(C)([O-])C.[K+]>>CN1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2N=CC=C2)=O | [CH3:1][N:2]1[C:3](=[O:4])[NH:5][CH2:6][c:7]2[cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15](-[n:16]4[cH:17][cH:18][cH:19][n:20]4)[cH:21][cH:22]3)[n:23][c:24]21>>[CH3:1][n:2]1[c:3](=[O:4])[n:5][cH:6][c:7]2[cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15](-[n:16]4[cH:17][cH:18][cH:19][n:20]4)[cH:21][cH:22]3)[n:2... | CN1C(=O)NCc2cnc(Nc3ccc(-n4cccn4)cc3)nc21 | Cn1c(=O)ncc2cnc(Nc3ccc(-n4cccn4)cc3)nc21 | null | null | O1CCCC1 | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccc(-n4cccn4)cc3)nc2[nH]1 | [C;D1;H3:1]-[N;H0;D3;+0:2]1-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[CH2;D2;+0:6]-[c:7]2:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2-1>>[C;D1;H3:1]-[n;H0;D3;+0:2]1:[c:12]2:[#7;a:11]:[c:10]:[#7;a:9]:[c:8]:[c:7]:2:[cH;D2;+0:6]:[n;H0;D2;+0:5]:[c;H0;D3;+0:3]:1=[O;D1;H0:4] | 69.4 | [{"value": 65.0, "product": "CN1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2N=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.4, "product": "CN1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2N=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Prepared from 200 mg (0.46 mmol) of 1-methyl-7-[4-(pyrazol-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, trifluoroacetic acid and 309 mg (2.76 mmol) of potassium tert-butoxide in 15 mL of tetrahydrofuran. The reaction mixture is stirred overnight. After the workup, the semi-solid is triturated in di... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | c1ncc2cncnc2n1.c1ccccc1.c1cn[nH]c1 | null | O1CCCC1 | null | 8 | CN1C(=O)NCc2cnc(Nc3ccc(-n4cccn4)cc3)nc21>O1CCCC1>Cn1c(=O)ncc2cnc(Nc3ccc(-n4cccn4)cc3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1558257c3ae1456980494b5eb3cc8d5d | COc1cc(N)cc(OC)c1.CSc1ncc(C=O)c(N)n1>>COc1cc(N=Cc2cnc(SC)nc2N)cc(OC)c1 | NC1=NC(=NC=C1C=O)SC.COC=1C=C(N)C=C(C1)OC.C(C)(=O)O>>COC=1C=C(C=C(C1)OC)N=CC=1C(=NC(=NC1)SC)N | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:17][c:18]([O:19][CH3:20])[cH:21]1.O=[CH:7][c:8]1[cH:9][n:10][c:11]([S:12][CH3:13])[n:14][c:15]1[NH2:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]=[CH:7][c:8]2[cH:9][n:10][c:11]([S:12][CH3:13])[n:14][c:15]2[NH2:16])[cH:17][c:18]([O:19][CH3:20])[cH:21]1 | COc1cc(N)cc(OC)c1.CSc1ncc(C=O)c(N)n1 | COc1cc(N=Cc2cnc(SC)nc2N)cc(OC)c1 | null | null | O | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | C(=Nc1ccccc1)c1cncnc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[N;D1;H2:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[N;D1;H2:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:1-[CH;D2;+0:1]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | 97.3 | [{"value": 96.0, "product": "COC=1C=C(C=C(C1)OC)N=CC=1C(=NC(=NC1)SC)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.3, "product": "COC=1C=C(C=C(C1)OC)N=CC=1C(=NC(=NC1)SC)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 8 | HOUR | To a suspension of 4.36 g (23.7 mmol) of 4-amino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (made as described in WO 98/33798) and 3.65 g (23.7 mmol) of 3,5-dimethoxyaniline in 165 mL of water was added 4.5 mL of glacial acetic acid. The reaction was stirred at 25° C. overnight and filtered. The filter pad was washed w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | c1ccccc1.c1cncnc1 | HO- | O | 25 | 8 | COc1cc(N)cc(OC)c1.CSc1ncc(C=O)c(N)n1>O>COc1cc(N=Cc2cnc(SC)nc2N)cc(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e910fbde0ea4406a22d1d0e036578c9 | CCNc1nc(SC)ncc1C=O.COc1cc(N)cc(OC)c1>>CCNc1nc(SC)ncc1C=Nc1cc(OC)cc(OC)c1 | C(C)NC1=NC(=NC=C1C=O)SC.COC=1C=C(N)C=C(C1)OC>>COC=1C=C(C=C(C1)OC)N=CC=1C(=NC(=NC1)SC)NCC | O=[CH:12][c:11]1[c:4]([NH:3][CH2:2][CH3:1])[n:5][c:6]([S:7][CH3:8])[n:9][cH:10]1.[NH2:13][c:14]1[cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]([O:21][CH3:22])[cH:23]1>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]([S:7][CH3:8])[n:9][cH:10][c:11]1[CH:12]=[N:13][c:14]1[cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]([O:21][CH3:22])[cH:23]1 | CCNc1nc(SC)ncc1C=O.COc1cc(N)cc(OC)c1 | CCNc1nc(SC)ncc1C=Nc1cc(OC)cc(OC)c1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | C(=Nc1ccccc1)c1cncnc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[#7:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[#7:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:1-[CH;D2;+0:1]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | 92 | [{"value": 92.0, "product": "COC=1C=C(C=C(C1)OC)N=CC=1C(=NC(=NC1)SC)NCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a stirred suspension of 4-ethylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (5.0 g, 25.09 mmol, made by the method described in J. Med. Chem., 1998; 41(17):3276-3292) and 3,5-dimethoxyaniline (3.84 g, 25.09 mmol) water (190 mL) was added glacial acetic acid (5 mL). The reaction mixture was stirred at ambient tem... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | c1cncnc1.c1ccccc1 | HO- | C(C)(=O)O | null | 24 | CCNc1nc(SC)ncc1C=O.COc1cc(N)cc(OC)c1>C(C)(=O)O>CCNc1nc(SC)ncc1C=Nc1cc(OC)cc(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-deb52e8a2d3b4d9fa5e2c6c955e224f1 | COc1cc(N=Cc2cnc(SC)nc2N)cc(OC)c1>>COc1cc(NCc2cnc(SC)nc2N)cc(OC)c1 | COC=1C=C(C=C(C1)OC)N=CC=1C(=NC(=NC1)SC)N.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>COC=1C=C(C=C(C1)OC)NCC=1C(=NC(=NC1)SC)N | [CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]=[CH:7][c:8]2[cH:9][n:10][c:11]([S:12][CH3:13])[n:14][c:15]2[NH2:16])[cH:17][c:18]([O:19][CH3:20])[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][CH2:7][c:8]2[cH:9][n:10][c:11]([S:12][CH3:13])[n:14][c:15]2[NH2:16])[cH:17][c:18]([O:19][CH3:20])[cH:21]1 | COc1cc(N=Cc2cnc(SC)nc2N)cc(OC)c1 | COc1cc(NCc2cnc(SC)nc2N)cc(OC)c1 | null | null | O1CCCC1 | Reduction | OtherReaction | d4a3c3af6b6e3a46274c741e9feddcd7af52a8fba8716af75123ec94a3d0151d | 469efbca661320a0d72c32f19625ec46edbc3ad7686cf46fdd0591eb136a8d7e | c1ccc(NCc2cncnc2)cc1 | [N;D1;H2:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[N;D1;H2:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH2;D2;+0:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | 91 | [{"value": 91.0, "product": "COC=1C=C(C=C(C1)OC)NCC=1C(=NC(=NC1)SC)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.0, "product": "COC=1C=C(C=C(C1)OC)NCC=1C(=NC(=NC1)SC)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 1.5 | HOUR | Into 18.2 mL (18.2 mmol) of a 1 M solution of lithium aluminum hydride (LAH) in tetrahydrofuran (THF) cooled to 5° C. was added a solution of 5.55 g (18.3 mmol) of 5-[(3,5-dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-ylamine in 94 mL of dry THF over 20 minutes. The reaction was stirred for 1.5 hours at 5... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Secondary amine | null | null | c1ccccc1.c1cncnc1 | null | O1CCCC1 | 5 | 1.5 | COc1cc(N=Cc2cnc(SC)nc2N)cc(OC)c1>O1CCCC1>COc1cc(NCc2cnc(SC)nc2N)cc(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ddce3a4f54045e88204069bd9a4fed3 | COc1cc(NCc2cnc(SC)nc2N)cc(OC)c1.O=C(n1ccnc1)n1ccnc1>>COc1cc(OC)cc(N2Cc3cnc(SC)nc3NC2=O)c1 | COC=1C=C(C=C(C1)OC)NCC=1C(=NC(=NC1)SC)N.[H-].[Na+].C(=O)(N1C=NC=C1)N1C=NC=C1>>COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)SC)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([NH:10][CH2:11][c:12]2[cH:13][n:14][c:15]([S:16][CH3:17])[n:18][c:19]2[NH2:20])[cH:23]1.c1cn([C:21](n2ccnc2)=[O:22])cn1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([N:10]2[CH2:11][c:12]3[cH:13][n:14][c:15]([S:16][CH3:17])[n:18][c:19]3[NH:20][C:21]2=[O:2... | COc1cc(NCc2cnc(SC)nc2N)cc(OC)c1.O=C(n1ccnc1)n1ccnc1 | COc1cc(OC)cc(N2Cc3cnc(SC)nc3NC2=O)c1 | null | null | CN(C=O)C | Acylation | OtherReaction | b87eea963c1c512c6e55e316d75ef273b11dda6ae8154eda8d6dab94e98f7cd8 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | O=C1Nc2ncncc2CN1c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12].[O;D1;H0:13]=[C;H0;D3;+0:14](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[O;D1;H0:13]=[C;H0;D3;+0:14]1-[NH;D2;+0:1]-[c:2]2:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:2-[C:8]-[N;H0;D3;+0:9]-1-[c:10](:[c:11]):[c:12] | 60 | [{"value": 60.0, "product": "COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)SC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.8, "product": "COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)SC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Into a solution of 5.0 g (16.3 mmol) of 5-[(3,5-dimethoxy-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-ylamine in 55 mL of dimethylformamide cooled to 5° C., was added 1.63 g (40.8 mmol) of sodium hydride as a 60% mineral oil suspension. The ice bath was removed, and the reaction was stirred for 1 hour. To the rea... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | c1ncc2c(n1)NC[NH]C2 | c1ccccc1.c1ncc2c(n1)NC[NH]C2 | Other | CN(C=O)C | null | 1 | COc1cc(NCc2cnc(SC)nc2N)cc(OC)c1.O=C(n1ccnc1)n1ccnc1>CN(C=O)C>COc1cc(OC)cc(N2Cc3cnc(SC)nc3NC2=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1fc1d0f6e1a44b70bf9dc9cc9623396a | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(SC)nc21.O=S(=O)(c1ccccc1)N1OC1c1ccccc1>>CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21 | COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)SC)CC)=O.C1(=CC=CC=C1)C1N(O1)S(=O)(=O)C1=CC=CC=C1>>COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)S(=O)C)CC)=O | [CH3:1][CH2:2][N:3]1[C:4](=[O:5])[N:6]([c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]([O:14][CH3:15])[cH:16]2)[CH2:17][c:18]2[cH:19][n:20][c:21]([S:22][CH3:23])[n:25][c:26]21.O=S(c1ccccc1)(N1OC1c1ccccc1)=[O:24]>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[N:6]([c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]([O:14][CH3:15])[cH:16]... | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(SC)nc21.O=S(=O)(c1ccccc1)N1OC1c1ccccc1 | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21 | null | null | ClCCl | Oxidation | Sulfanyl to sulfinyl_sulfonyl | 7bfca6b2d91e829a54b6d67114560b32481fd75fada7e7003fe3ba4671c4f594 | 1135622d483cd7dfdd7dfec13000528bd6a6736fbb03e0ce07273fb1059c002d | O=C1Nc2ncncc2CN1c1ccccc1 | O=S(=[O;H0;D1;+0:1])(-N1-O-C-1-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[#7:2]-[c:3]:[#7;a:4]:[c:5](-[S;H0;D2;+0:6]-[C;D1;H3:7]):[#7;a:8]:[c:9]>>[#7:2]-[c:3]:[#7;a:4]:[c:5](-[S;H0;D3;+0:6](-[C;D1;H3:7])=[O;H0;D1;+0:1]):[#7;a:8]:[c:9] | 78.5 | [{"value": 78.0, "product": "COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)S(=O)C)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.5, "product": "COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)S(=O)C)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 3-(3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfanyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one (5.61 g, 15.57 mmol) in dichloromethane (100 mL) at ambient temperature was added 3-phenyl-2-(phenylsulfonyl)oxaziridine (4.88 g, 18.69 mmol, PD 0191006, Org. Synth., 1987; 66:203-210) in portions. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Monosulfide | Sulfoxide | c1ccccc1.C1NO1.c1ccccc1 | null | c1ccccc1.c1ncc2c(n1)[NH]C[NH]C2 | HO- | ClCCl | null | 8 | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(SC)nc21.O=S(=O)(c1ccccc1)N1OC1c1ccccc1>ClCCl>CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53c699833672443fa5a96b07a82b473a | CCN(CC)CCCCN.COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1>>CCN(CC)CCCCNc1ncc2c(n1)NC(=O)N(c1cc(OC)cc(OC)c1)C2 | COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)S(=O)C)=O.C(C)N(CC)CCCCN.C(C)N(CC)CCCCN.C12(C(=O)CC(CC1)C2(C)C)CS(=O)(=O)O>>C(C)N(CCCCNC1=NC=C2C(=N1)NC(N(C2)C2=CC(=CC(=C2)OC)OC)=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][NH2:10].CS(=O)[c:11]1[n:12][cH:13][c:14]2[c:15]([n:16]1)[NH:17][C:18](=[O:19])[N:20]([c:21]1[cH:22][c:23]([O:24][CH3:25])[cH:26][c:27]([O:28][CH3:29])[cH:30]1)[CH2:31]2>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]1[n:12][cH... | CCN(CC)CCCCN.COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1 | CCN(CC)CCCCNc1ncc2c(n1)NC(=O)N(c1cc(OC)cc(OC)c1)C2 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 9eec07683599b8d4325d4d1e1eb43e690bb91719380e2297c71a6c075c5bf179 | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1Nc2ncncc2CN1c1ccccc1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:2]:[c:3] | 62.1 | [{"value": 62.0, "product": "C(C)N(CCCCNC1=NC=C2C(=N1)NC(N(C2)C2=CC(=CC(=C2)OC)OC)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.1, "product": "C(C)N(CCCCNC1=NC=C2C(=N1)NC(N(C2)C2=CC(=CC(=C2)OC)OC)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 8 | HOUR | A suspension of 0.2261 g (0.65 mmol) of 3-(3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.103 g (0.71 mmol) of diethylaminobutylamine in 10 mL of dry dioxane was warmed to 60° C. and stirred overnight. To the reaction mixture was added 0.306 g (2.13 mmol) of diethylaminobut... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)NC[NH]C2 | c1ncc2c(n1)NC[NH]C2 | c1ncc2c(n1)NC[NH]C2.c1ccccc1 | Other | O1CCOCC1 | 60 | 8 | CCN(CC)CCCCN.COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1>O1CCOCC1>CCN(CC)CCCCNc1ncc2c(n1)NC(=O)N(c1cc(OC)cc(OC)c1)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf021851595c400e8dd96764b8eda5ba | CCN(CC)CCCCN.CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21>>CCN(CC)CCCCNc1ncc2c(n1)N(CC)C(=O)N(c1cc(OC)cc(OC)c1)C2 | COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)S(=O)C)CC)=O.C(C)N(CCCCN)CC.FC(C(=O)O)(F)F>>C(C)N(CCCCNC1=NC=C2C(=N1)N(C(N(C2)C2=CC(=CC(=C2)OC)OC)=O)CC)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][NH2:10].CS(=O)[c:11]1[n:12][cH:13][c:14]2[c:15]([n:16]1)[N:17]([CH2:18][CH3:19])[C:20](=[O:21])[N:22]([c:23]1[cH:24][c:25]([O:26][CH3:27])[cH:28][c:29]([O:30][CH3:31])[cH:32]1)[CH2:33]2>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][CH2:9][NH:10... | CCN(CC)CCCCN.CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21 | CCN(CC)CCCCNc1ncc2c(n1)N(CC)C(=O)N(c1cc(OC)cc(OC)c1)C2 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | dfe6b1334374df9b6c179328698ff0f8ea7eb4b492ffbd39f9a2e4f3dfb4cb25 | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1Nc2ncncc2CN1c1ccccc1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:2]:[c:3] | 56 | [{"value": 56.0, "product": "C(C)N(CCCCNC1=NC=C2C(=N1)N(C(N(C2)C2=CC(=CC(=C2)OC)OC)=O)CC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.0, "product": "C(C)N(CCCCNC1=NC=C2C(=N1)N(C(N(C2)C2=CC(=CC(=C2)OC)OC)=O)CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of 3-(3,5-dimethoxy-phenyl)-1-ethyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one (0.5 g, 1.33 mmol), 4-diethylaminobutylamine (0.38 g, 2.66 mmol,) and trifluoroacetic acid (0.31 g, 2.66 mmol) in acetonitrile (6 mL) was heated in a sealed tube at 90° C. for 18 hours. The solvent was removed... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)[NH]C[NH]C2 | c1ncc2c(n1)[NH]C[NH]C2 | c1ncc2c(n1)[NH]C[NH]C2.c1ccccc1 | Other | C(C)#N | 90 | null | CCN(CC)CCCCN.CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21>C(C)#N>CCN(CC)CCCCNc1ncc2c(n1)N(CC)C(=O)N(c1cc(OC)cc(OC)c1)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c1f44645dbe44dbabe802671fe569be | CCN(CC)CCOc1ccc(N)cc1.CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21>>CCN(CC)CCOc1ccc(Nc2ncc3c(n2)N(CC)C(=O)N(c2cc(OC)cc(OC)c2)C3)cc1 | COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)S(=O)C)CC)=O.C(C)N(CCOC1=CC=C(N)C=C1)CC.FC(C(=O)O)(F)F.C(C)N(CC)CC.O(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>C(C)N(CCOC1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(N(C2)C2=CC(=CC(=C2)OC)OC)=O)CC)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:37][cH:38]1.CS(=O)[c:14]1[n:15][cH:16][c:17]2[c:18]([n:19]1)[N:20]([CH2:21][CH3:22])[C:23](=[O:24])[N:25]([c:26]1[cH:27][c:28]([O:29][CH3:30])[cH:31][c:32]([O:33][CH3:34])[cH:35]1)[CH2:36]2>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])... | CCN(CC)CCOc1ccc(N)cc1.CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21 | CCN(CC)CCOc1ccc(Nc2ncc3c(n2)N(CC)C(=O)N(c2cc(OC)cc(OC)c2)C3)cc1 | null | null | CCCCCC.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | dfe6b1334374df9b6c179328698ff0f8ea7eb4b492ffbd39f9a2e4f3dfb4cb25 | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1Nc2nc(Nc3ccccc3)ncc2CN1c1ccccc1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | 81 | [{"value": 81.0, "product": "C(C)N(CCOC1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(N(C2)C2=CC(=CC(=C2)OC)OC)=O)CC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "C(C)N(CCOC1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(N(C2)C2=CC(=CC(=C2)OC)OC)=O)CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 4 | HOUR | A mixture of 3-(3,5-dimethoxy-phenyl)-1-ethyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one (0.5 g, 1.33 mmol), 4-(2-diethylaminoethoxy)aniline (0.55 g, 2.66 mmol, Helv. Chim. Acta, 1960; 43:1971-1979) and trifluoroacetic acid (0.46 g, 3.98 mmol) in acetonitrile (6 mL) was heated in a sealed tube at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)[NH]C[NH]C2 | c1ncc2c(n1)[NH]C[NH]C2 | c1ccccc1.c1ncc2c(n1)[NH]C[NH]C2.c1ccccc1 | Other | CCCCCC.C(C)#N | 100 | 4 | CCN(CC)CCOc1ccc(N)cc1.CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21>CCCCCC.C(C)#N>CCN(CC)CCOc1ccc(Nc2ncc3c(n2)N(CC)C(=O)N(c2cc(OC)cc(OC)c2)C3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8a55f3cc85c462eb471a80e5bf6fbdd | COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1.NCCNCc1ccncc1>>COc1cc(OC)cc(N2Cc3cnc(NCCNCc4ccncc4)nc3NC2=O)c1 | COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)S(=O)C)=O.N1=CC=C(C=C1)CNCCN>>COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)NCCNCC1=CC=NC=C1)=O | CS(=O)[c:15]1[n:14][cH:13][c:12]2[c:28]([n:27]1)[NH:29][C:30](=[O:31])[N:10]([c:9]1[cH:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:32]1)[CH2:11]2.[NH2:16][CH2:17][CH2:18][NH:19][CH2:20][c:21]1[cH:22][cH:23][n:24][cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([N:10]2[CH2:11][c:12]3[cH:13][... | COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1.NCCNCc1ccncc1 | COc1cc(OC)cc(N2Cc3cnc(NCCNCc4ccncc4)nc3NC2=O)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 9eec07683599b8d4325d4d1e1eb43e690bb91719380e2297c71a6c075c5bf179 | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1Nc2nc(NCCNCc3ccncc3)ncc2CN1c1ccccc1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:2]:[c:3] | 13 | [{"value": 13.0, "product": "COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)NCCNCC1=CC=NC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the general procedure above, 3-(3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.1423 g (0.941 mmol) of N-(4-picoly)ethylenediamine were reacted. The residue was chromatographed eluting with ethyl acetate/ethanol/triethylamine (9:2:1 v/v/v) then ethyl acetate/ethanol/tr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)NC[NH]C2 | c1ncc2c(n1)NC[NH]C2 | c1ccccc1.c1ncc2c(n1)NC[NH]C2.c1ccncc1 | Other | null | null | null | COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1.NCCNCc1ccncc1>>COc1cc(OC)cc(N2Cc3cnc(NCCNCc4ccncc4)nc3NC2=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-deea4f004870422fb9b4171758a1f583 | CN1CCN(CCCCN)CC1.COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1>>COc1cc(OC)cc(N2Cc3cnc(NCCCCN4CCN(C)CC4)nc3NC2=O)c1 | COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)S(=O)C)=O.CN1CCN(CC1)CCCCN>>COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)NCCCCN1CCN(CC1)C)=O | [NH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][N:24]([CH3:25])[CH2:26][CH2:27]1.CS(=O)[c:15]1[n:14][cH:13][c:12]2[c:29]([n:28]1)[NH:30][C:31](=[O:32])[N:10]([c:9]1[cH:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:33]1)[CH2:11]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([N:10]2[CH2:11]... | CN1CCN(CCCCN)CC1.COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1 | COc1cc(OC)cc(N2Cc3cnc(NCCCCN4CCN(C)CC4)nc3NC2=O)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 9eec07683599b8d4325d4d1e1eb43e690bb91719380e2297c71a6c075c5bf179 | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1Nc2nc(NCCCCN3CCNCC3)ncc2CN1c1ccccc1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:2]:[c:3] | 31 | [{"value": 31.0, "product": "COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)NCCCCN1CCN(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the general procedure above, 3-(3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.1354 g (0.791 mmol) of 4-(4-methyl-piperazin-1-yl)-butylamine were reacted. The residue was chromatographed over silica gel, eluting with ethyl acetate/ethanol/triethylamine (9:2:1 v/v/v) t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)NC[NH]C2 | c1ncc2c(n1)NC[NH]C2 | c1ccccc1.c1ncc2c(n1)NC[NH]C2.C1C[NH]CC[NH]1 | Other | null | null | null | CN1CCN(CCCCN)CC1.COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1>>COc1cc(OC)cc(N2Cc3cnc(NCCCCN4CCN(C)CC4)nc3NC2=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2d3339fb8f3646d5a7bb0f62554ba8ee | CN1CCN(CCCCCN)CC1.COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1>>COc1cc(OC)cc(N2Cc3cnc(NCCCCCN4CCN(C)CC4)nc3NC2=O)c1 | COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)S(=O)C)=O.CN1CCN(CC1)CCCCCN>>COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)NCCCCCN1CCN(CC1)C)=O | [NH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]1.CS(=O)[c:15]1[n:14][cH:13][c:12]2[c:30]([n:29]1)[NH:31][C:32](=[O:33])[N:10]([c:9]1[cH:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:34]1)[CH2:11]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([N:10]2... | CN1CCN(CCCCCN)CC1.COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1 | COc1cc(OC)cc(N2Cc3cnc(NCCCCCN4CCN(C)CC4)nc3NC2=O)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 9eec07683599b8d4325d4d1e1eb43e690bb91719380e2297c71a6c075c5bf179 | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1Nc2nc(NCCCCCN3CCNCC3)ncc2CN1c1ccccc1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:2]:[c:3] | 24 | [{"value": 24.0, "product": "COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)NCCCCCN1CCN(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the general procedure above, 3-(3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.1475 g (0.805 mmol) of 5-(4-methyl-piperazin-1-yl)-pentylamine were reacted. The residue was chromatographed over silica gel, eluting with ethyl acetate/ethanol/triethylamine (9:2:1 v/v/v) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)NC[NH]C2 | c1ncc2c(n1)NC[NH]C2 | c1ccccc1.c1ncc2c(n1)NC[NH]C2.C1C[NH]CC[NH]1 | Other | null | null | null | CN1CCN(CCCCCN)CC1.COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1>>COc1cc(OC)cc(N2Cc3cnc(NCCCCCN4CCN(C)CC4)nc3NC2=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-05819feff3b64c408fca4cd71fa216c9 | CCN(CC)CCCN.COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1>>CCN(CC)CCCNc1ncc2c(n1)NC(=O)N(c1cc(OC)cc(OC)c1)C2 | COC=1C=C(C=C(C1)OC)N1C(NC2=NC(=NC=C2C1)S(=O)C)=O.C(C)N(CC)CCCN>>C(C)N(CCCNC1=NC=C2C(=N1)NC(N(C2)C2=CC(=CC(=C2)OC)OC)=O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH2:9].CS(=O)[c:10]1[n:11][cH:12][c:13]2[c:14]([n:15]1)[NH:16][C:17](=[O:18])[N:19]([c:20]1[cH:21][c:22]([O:23][CH3:24])[cH:25][c:26]([O:27][CH3:28])[cH:29]1)[CH2:30]2>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH:9][c:10]1[n:11][cH:12][c:13]2[c:14... | CCN(CC)CCCN.COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1 | CCN(CC)CCCNc1ncc2c(n1)NC(=O)N(c1cc(OC)cc(OC)c1)C2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 9eec07683599b8d4325d4d1e1eb43e690bb91719380e2297c71a6c075c5bf179 | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1Nc2ncncc2CN1c1ccccc1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:2]:[c:3] | 40 | [{"value": 40.0, "product": "C(C)N(CCCNC1=NC=C2C(=N1)NC(N(C2)C2=CC(=CC(=C2)OC)OC)=O)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the general procedure above, 3-(3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.1121 g (0.861 mmol) of diethylaminopropylamine were reacted. The residue was chromatographed eluting with acetonitrile/ethanol/triethylamine (8:1:0.5 v/v/v) to give 0.0476 g (40%) of the ti... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)NC[NH]C2 | c1ncc2c(n1)NC[NH]C2 | c1ncc2c(n1)NC[NH]C2.c1ccccc1 | Other | null | null | null | CCN(CC)CCCN.COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1>>CCN(CC)CCCNc1ncc2c(n1)NC(=O)N(c1cc(OC)cc(OC)c1)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-632b69901e9e4e698027302c6fb24b21 | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21.NCCNCc1ccncc1>>CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(NCCNCc3ccncc3)nc21 | COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)S(=O)C)CC)=O.N1=CC=C(C=C1)CNCCN>>COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)NCCNCC1=CC=NC=C1)CC)=O | CS(=O)[c:21]1[n:20][cH:19][c:18]2[c:34]([n:33]1)[N:3]([CH2:2][CH3:1])[C:4](=[O:5])[N:6]([c:7]1[cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]([O:14][CH3:15])[cH:16]1)[CH2:17]2.[NH2:22][CH2:23][CH2:24][NH:25][CH2:26][c:27]1[cH:28][cH:29][n:30][cH:31][cH:32]1>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[N:6]([c:7]2[cH:8][c:9]([O:10][CH3:... | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21.NCCNCc1ccncc1 | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(NCCNCc3ccncc3)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dfe6b1334374df9b6c179328698ff0f8ea7eb4b492ffbd39f9a2e4f3dfb4cb25 | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1Nc2nc(NCCNCc3ccncc3)ncc2CN1c1ccccc1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:2]:[c:3] | 25 | [{"value": 25.0, "product": "COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)NCCNCC1=CC=NC=C1)CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the general procedure above, 3-(3,5-dimethoxy-phenyl)-1-ethyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.1317 g (0.871 mmol) of N-(4-picolyl)ethylenediamine were reacted. The residue was chromatographed over silica gel, eluting with ethyl acetate/ethanol/triethylamine (9:2:1 v/v/v), to... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)[NH]C[NH]C2 | c1ncc2c(n1)[NH]C[NH]C2 | c1ccccc1.c1ncc2c(n1)[NH]C[NH]C2.c1ccncc1 | Other | null | null | null | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21.NCCNCc1ccncc1>>CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(NCCNCc3ccncc3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea5d8470cf3043a3805c830ab12a5550 | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21.CN1CCN(CCCN)CC1>>CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(NCCCN3CCN(C)CC3)nc21 | COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)S(=O)C)CC)=O.CN1CCN(CC1)CCCN>>COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)NCCCN1CCN(CC1)C)CC)=O | CS(=O)[c:21]1[n:20][cH:19][c:18]2[c:34]([n:33]1)[N:3]([CH2:2][CH3:1])[C:4](=[O:5])[N:6]([c:7]1[cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]([O:14][CH3:15])[cH:16]1)[CH2:17]2.[NH2:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:27][CH2:28][N:29]([CH3:30])[CH2:31][CH2:32]1>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[N:6]([c:7]2[cH:8][c:9]([O:1... | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21.CN1CCN(CCCN)CC1 | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(NCCCN3CCN(C)CC3)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dfe6b1334374df9b6c179328698ff0f8ea7eb4b492ffbd39f9a2e4f3dfb4cb25 | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1Nc2nc(NCCCN3CCNCC3)ncc2CN1c1ccccc1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:2]:[c:3] | 57 | [{"value": 57.0, "product": "COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)NCCCN1CCN(CC1)C)CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the general procedure above, 3-(3,5-dimethoxy-phenyl)-1-ethyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.1142 g (0.726 mmol) of 3-(4-methyl-piperazin-1-yl)-propylamine were reacted. The residue was chromatographed over silica gel, eluting with ethyl acetate/ethanol/triethylamine (9:2:1... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)[NH]C[NH]C2 | c1ncc2c(n1)[NH]C[NH]C2 | c1ccccc1.c1ncc2c(n1)[NH]C[NH]C2.C1C[NH]CC[NH]1 | Other | null | null | null | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21.CN1CCN(CCCN)CC1>>CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(NCCCN3CCN(C)CC3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9adf27b52734687b8682fddc049617a | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21.CN1CCN(CCCCN)CC1>>CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(NCCCCN3CCN(C)CC3)nc21 | COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)S(=O)C)CC)=O.CN1CCN(CC1)CCCCN>>COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)NCCCCN1CCN(CC1)C)CC)=O | CS(=O)[c:21]1[n:20][cH:19][c:18]2[c:35]([n:34]1)[N:3]([CH2:2][CH3:1])[C:4](=[O:5])[N:6]([c:7]1[cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]([O:14][CH3:15])[cH:16]1)[CH2:17]2.[NH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][N:30]([CH3:31])[CH2:32][CH2:33]1>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[N:6]([c:7]2[cH:8][c... | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21.CN1CCN(CCCCN)CC1 | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(NCCCCN3CCN(C)CC3)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dfe6b1334374df9b6c179328698ff0f8ea7eb4b492ffbd39f9a2e4f3dfb4cb25 | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1Nc2nc(NCCCCN3CCNCC3)ncc2CN1c1ccccc1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:2]:[c:3] | 41 | [{"value": 41.0, "product": "COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)NCCCCN1CCN(CC1)C)CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the general procedure above, 3-(3,5-dimethoxy-phenyl)-1-ethyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.1253 g (0.732 mmol) of 4-(4-methyl-piperazin-1-yl)-butylamine were reacted. The residue was chromatographed over silica gel, eluting with ethyl acetate/ethanol/triethylamine (9:2:1 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)[NH]C[NH]C2 | c1ncc2c(n1)[NH]C[NH]C2 | c1ccccc1.c1ncc2c(n1)[NH]C[NH]C2.C1C[NH]CC[NH]1 | Other | null | null | null | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21.CN1CCN(CCCCN)CC1>>CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(NCCCCN3CCN(C)CC3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6103ca4d6d98461398cd56109f4a0309 | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21.CN1CCN(CCCCCN)CC1>>CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(NCCCCCN3CCN(C)CC3)nc21 | COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)S(=O)C)CC)=O.CN1CCN(CC1)CCCCCN>>COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)NCCCCCN1CCN(CC1)C)CC)=O | CS(=O)[c:21]1[n:20][cH:19][c:18]2[c:36]([n:35]1)[N:3]([CH2:2][CH3:1])[C:4](=[O:5])[N:6]([c:7]1[cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]([O:14][CH3:15])[cH:16]1)[CH2:17]2.[NH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH2:34]1>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[N:6]([c:7]2... | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21.CN1CCN(CCCCCN)CC1 | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(NCCCCCN3CCN(C)CC3)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dfe6b1334374df9b6c179328698ff0f8ea7eb4b492ffbd39f9a2e4f3dfb4cb25 | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1Nc2nc(NCCCCCN3CCNCC3)ncc2CN1c1ccccc1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:2]:[c:3] | 31 | [{"value": 31.0, "product": "COC=1C=C(C=C(C1)OC)N1C(N(C2=NC(=NC=C2C1)NCCCCCN1CCN(CC1)C)CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the general procedure above, 3-(3,5-dimethoxy-phenyl)-1-ethyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.1365 g (0.745 mmol) of 5-(4-methyl-piperazin-1-yl)-pentylamine were reacted. The residue was chromatographed over silica gel, eluting with ethyl acetate/ethanol/triethylamine (9:2:1... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)[NH]C[NH]C2 | c1ncc2c(n1)[NH]C[NH]C2 | c1ccccc1.c1ncc2c(n1)[NH]C[NH]C2.C1C[NH]CC[NH]1 | Other | null | null | null | CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(S(C)=O)nc21.CN1CCN(CCCCCN)CC1>>CCN1C(=O)N(c2cc(OC)cc(OC)c2)Cc2cnc(NCCCCCN3CCN(C)CC3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71d7361537f840fea2093b24cf35b4c3 | COC(=O)c1cc(OC)cc(OC)c1Cl>>COc1cc(OC)c(Cl)c(C(=O)O)c1 | COC(C1=C(C(=CC(=C1)OC)OC)Cl)=O.[OH-].[K+]>>ClC1=C(C(=O)O)C=C(C=C1OC)OC | C[O:13][C:11]([c:10]1[c:8]([Cl:9])[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:14]1)=[O:12]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([Cl:9])[c:10]([C:11](=[O:12])[OH:13])[cH:14]1 | COC(=O)c1cc(OC)cc(OC)c1Cl | COc1cc(OC)c(Cl)c(C(=O)O)c1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 87.2 | [{"value": 87.0, "product": "ClC1=C(C(=O)O)C=C(C=C1OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.2, "product": "ClC1=C(C(=O)O)C=C(C=C1OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Into a solution of 12 g (52.0 mmol) of 2-chloro-3,5-dimethoxy-benzoic acid methyl ester (prepared according to the method of T. R. Kasturi and E. M. Abraham, Indian Journal of Chemistry, 1973; 11:1099-1104) in 40 mL of methanol was added 60 mL (60 mmol) of 1N potassium hydroxide solution. After stirring overnight at ro... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO | null | 8 | COC(=O)c1cc(OC)cc(OC)c1Cl>CO>COc1cc(OC)c(Cl)c(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c3a6f3ab0ce4779a84e24dab0f73ba6 | CC(C)(C)O.COc1cc(OC)c(Cl)c(C(=O)O)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>COc1cc(NC(=O)OC(C)(C)C)c(Cl)c(OC)c1 | C(C)(C)(C)O.ClC1=C(C(=O)O)C=C(C=C1OC)OC.C(C)N(CC)CC.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-]>>ClC1=C(C=C(C=C1OC)OC)NC(OC(C)(C)C)=O | [OH:9][C:10]([CH3:11])([CH3:12])[CH3:13].O[C:7]([c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:19][c:16]([O:17][CH3:18])[c:14]1[Cl:15])=[O:8].[N-]=[N+]=[N:6]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]([Cl:15])[c:16]([O:17][CH3:18])[cH:19]1 | CC(C)(C)O.COc1cc(OC)c(Cl)c(C(=O)O)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | COc1cc(NC(=O)OC(C)(C)C)c(Cl)c(OC)c1 | null | null | C1(=CC=CC=C1)C | Protection | OtherReaction | 8649defade347839fb6465f2df728b649c3f18216370d2ec3a4df80a09647168 | b944663b5278c281edc6c72611c69e4309c3f5728dcd63d51413085e18c1d2e7 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[Cl;D1;H0:7]):[c:8].O=P(-[N;H0;D2;+0:9]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C;D1;H3:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[OH;D1;+0:14]>>[C;D1;H3:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[O;H0;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:... | 64 | [{"value": 64.0, "product": "ClC1=C(C=C(C=C1OC)OC)NC(OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.0, "product": "ClC1=C(C=C(C=C1OC)OC)NC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a solution of 9.57 g (44.18 mmol) of 2-chloro-3,5-dimethoxy-benzoic acid and 4.78 g (47.3 mmol) of triethylamine in 250 mL of toluene was added 13.57 g (49.3 mmol) diphenylphosphoryl azide. The reaction was refluxed for 4 hours. To the reaction was added 3.63 g (49.0 mmol) of tert-butanol. The reaction was refluxe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Tertiary alcohol | Carbamic ester.Ether.Boc | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CC(C)(C)O.COc1cc(OC)c(Cl)c(C(=O)O)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C>COc1cc(NC(=O)OC(C)(C)C)c(Cl)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c7d2e9ad817e419e9dccae79ac1fec04 | COc1cc(NC(=O)OC(C)(C)C)c(Cl)c(OC)c1>>COc1cc(N)c(Cl)c(OC)c1 | C(C)(C)(C)OC(NC1=C(C(=CC(=C1)OC)OC)Cl)=O.FC(C(=O)O)(F)F>>ClC1=C(C=C(C=C1OC)OC)N | CC(C)(C)OC(=O)[NH:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:12][c:9]([O:10][CH3:11])[c:7]1[Cl:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([Cl:8])[c:9]([O:10][CH3:11])[cH:12]1 | COc1cc(NC(=O)OC(C)(C)C)c(Cl)c(OC)c1 | COc1cc(N)c(Cl)c(OC)c1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 101,012.8 | [{"value": 101012.8, "product": "ClC1=C(C=C(C=C1OC)OC)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To 6.01 g (0.021 mmol) of (2-chloro-3,5-dimethoxy-phenyl)-carbamic acid tert-butyl ester was added 15 mL of trifluoroacetic acid. The reaction was stirred for 3 hours at room temperature, then concentrated in vacuo. The residue was made basic with a saturated solution of sodium bicarbonate, then extracted three times w... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | null | null | 3 | COc1cc(NC(=O)OC(C)(C)C)c(Cl)c(OC)c1>>COc1cc(N)c(Cl)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5db665303cbf4edca956a9ab3e11c1fe | CCNc1nc(SC)ncc1C=O.COc1cc(N)c(Cl)c(OC)c1>>CCNc1nc(SC)ncc1C=Nc1cc(OC)cc(OC)c1Cl | ClC1=C(C=C(C=C1OC)OC)N.C(C)NC1=NC(=NC=C1C=O)SC>>ClC1=C(C=C(C=C1OC)OC)N=CC=1C(=NC(=NC1)SC)NCC | O=[CH:12][c:11]1[c:4]([NH:3][CH2:2][CH3:1])[n:5][c:6]([S:7][CH3:8])[n:9][cH:10]1.[NH2:13][c:14]1[cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]([O:21][CH3:22])[c:23]1[Cl:24]>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]([S:7][CH3:8])[n:9][cH:10][c:11]1[CH:12]=[N:13][c:14]1[cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]([O:21][CH3:22])[c... | CCNc1nc(SC)ncc1C=O.COc1cc(N)c(Cl)c(OC)c1 | CCNc1nc(SC)ncc1C=Nc1cc(OC)cc(OC)c1Cl | null | S(O)(O)(=O)=O | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | C(=Nc1ccccc1)c1cncnc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[#7:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[#7:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:1-[CH;D2;+0:1]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | 99.6 | [{"value": 93.0, "product": "ClC1=C(C=C(C=C1OC)OC)N=CC=1C(=NC(=NC1)SC)NCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.6, "product": "ClC1=C(C=C(C=C1OC)OC)N=CC=1C(=NC(=NC1)SC)NCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Into a solution of 3.78 g (20.2 mmol) of 2-chloro-3,5-dimethoxy-phenylamine in 110 mL of toluene was added 3.97 g (20.15 mmol) of 4-ethylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde. The reaction vessel was equipped with a Dean-Stark trap, and the reaction was warmed to reflux. After 3 hours, two drops of concentra... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | c1cncnc1.c1ccccc1 | HO- | S(O)(O)(=O)=O.C1(=CC=CC=C1)C | null | 3 | CCNc1nc(SC)ncc1C=O.COc1cc(N)c(Cl)c(OC)c1>S(O)(O)(=O)=O.C1(=CC=CC=C1)C>CCNc1nc(SC)ncc1C=Nc1cc(OC)cc(OC)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b699cc9d2df54c71a416343e78e617c1 | CCNc1nc(SC)ncc1C=Nc1cc(OC)cc(OC)c1Cl>>CCNc1nc(SC)ncc1CNc1cc(OC)cc(OC)c1Cl | [H-].[H-].[H-].[H-].[Li+].[Al+3].ClC1=C(C=C(C=C1OC)OC)N=CC=1C(=NC(=NC1)SC)NCC>>ClC1=C(C=C(C=C1OC)OC)NCC=1C(=NC(=NC1)SC)NCC | [CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]([S:7][CH3:8])[n:9][cH:10][c:11]1[CH:12]=[N:13][c:14]1[cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]([O:21][CH3:22])[c:23]1[Cl:24]>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]([S:7][CH3:8])[n:9][cH:10][c:11]1[CH2:12][NH:13][c:14]1[cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]([O:21][CH3:22])[c:23]1... | CCNc1nc(SC)ncc1C=Nc1cc(OC)cc(OC)c1Cl | CCNc1nc(SC)ncc1CNc1cc(OC)cc(OC)c1Cl | null | null | C1CCOC1 | Reduction | OtherReaction | d4a3c3af6b6e3a46274c741e9feddcd7af52a8fba8716af75123ec94a3d0151d | 469efbca661320a0d72c32f19625ec46edbc3ad7686cf46fdd0591eb136a8d7e | c1ccc(NCc2cncnc2)cc1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH2;D2;+0:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | 74 | [{"value": 74.0, "product": "ClC1=C(C=C(C=C1OC)OC)NCC=1C(=NC(=NC1)SC)NCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.6, "product": "ClC1=C(C=C(C=C1OC)OC)NCC=1C(=NC(=NC1)SC)NCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 1 | HOUR | Into a suspension of 6.96 g (18.97 mmol) of {5-[(2-chloro-3,5-dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-ethyl-amine in 200 mL of dry THF cooled to 5° C. was added 18.97 mL (18.97 mmol) of a 1 M solution of LAH in THF. After stirring for 1 hour, the cold reaction was quenched by sequential addition... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Secondary amine | null | null | c1cncnc1.c1ccccc1 | null | C1CCOC1 | 5 | 1 | CCNc1nc(SC)ncc1C=Nc1cc(OC)cc(OC)c1Cl>C1CCOC1>CCNc1nc(SC)ncc1CNc1cc(OC)cc(OC)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7f13c0bddef486baca10e821bbee899 | CCNc1nc(SC)ncc1CNc1cc(OC)cc(OC)c1Cl.O=C(n1ccnc1)n1ccnc1>>CCN1C(=O)N(c2cc(OC)cc(OC)c2Cl)Cc2cnc(SC)nc21 | ClC1=C(C=C(C=C1OC)OC)NCC=1C(=NC(=NC1)SC)NCC.[H-].[Na+].C(=O)(N1C=NC=C1)N1C=NC=C1>>ClC1=C(C=C(C=C1OC)OC)N1C(N(C2=NC(=NC=C2C1)SC)CC)=O | [CH3:1][CH2:2][NH:3][c:26]1[c:19]([CH2:18][NH:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]([O:14][CH3:15])[c:16]2[Cl:17])[cH:20][n:21][c:22]([S:23][CH3:24])[n:25]1.c1cn([C:4](n2ccnc2)=[O:5])cn1>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[N:6]([c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]([O:14][CH3:15])[c:16]2[Cl:17])[CH2:... | CCNc1nc(SC)ncc1CNc1cc(OC)cc(OC)c1Cl.O=C(n1ccnc1)n1ccnc1 | CCN1C(=O)N(c2cc(OC)cc(OC)c2Cl)Cc2cnc(SC)nc21 | null | null | CN(C)C=O | Acylation | OtherReaction | 80d058b6533bd31bc9bd830721d0afaecb92fe03207242d2b799f3fe12fc25ad | bf5bab008aedc534107e4f090e82dcd18197098a48ec0ce73cbefdfec414069e | O=C1Nc2ncncc2CN1c1ccccc1 | [C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1-[C:10]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14].[O;D1;H0:15]=[C;H0;D3;+0:16](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C;D1;H3:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:16](=[O;D1;H0:15])-[N;H0;D3;+0:11](-[c:12](:[c:13]):[c:14])-[C:10]-[c:9]2:[c:8]:[#7;a:7]:[c:6]:[... | 70.2 | [{"value": 70.0, "product": "ClC1=C(C=C(C=C1OC)OC)N1C(N(C2=NC(=NC=C2C1)SC)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.2, "product": "ClC1=C(C=C(C=C1OC)OC)N1C(N(C2=NC(=NC=C2C1)SC)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Into a solution of 1.00 g (2.71 mmol) of {5-[(2-chloro-3,5-dimethoxy-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-ethyl-amine in 7 mL of dry DMF cooled to 5° C. was added 0.271 g (6.78 mmol) of sodium hydride as a 60% mineral oil suspension. The ice bath was removed, and the reaction was stirred for 1 hour. To... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | c1ncc2c(n1)[NH]C[NH]C2 | c1ccccc1.c1ncc2c(n1)[NH]C[NH]C2 | Other | CN(C)C=O | null | 1 | CCNc1nc(SC)ncc1CNc1cc(OC)cc(OC)c1Cl.O=C(n1ccnc1)n1ccnc1>CN(C)C=O>CCN1C(=O)N(c2cc(OC)cc(OC)c2Cl)Cc2cnc(SC)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03de9b8b252b48fab13a5348d20f8b57 | COc1cc(NCc2cnc(SC)nc2N)cc(OC)c1.N#CBr>>COc1cc(OC)cc(N2Cc3cnc(SC)nc3N=C2N)c1 | COC=1C=C(C=C(C1)OC)NCC=1C(=NC(=NC1)SC)N.N#CBr.N#CBr>>COC=1C=C(C=C(C1)OC)N1C(=NC2=NC(=NC=C2C1)SC)N | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([NH:10][CH2:11][c:12]2[cH:13][n:14][c:15]([S:16][CH3:17])[n:18][c:19]2[NH2:20])[cH:23]1.Br[C:21]#[N:22]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([N:10]2[CH2:11][c:12]3[cH:13][n:14][c:15]([S:16][CH3:17])[n:18][c:19]3[N:20]=[C:21]2[NH2:22])[cH:23]1 | COc1cc(NCc2cnc(SC)nc2N)cc(OC)c1.N#CBr | COc1cc(OC)cc(N2Cc3cnc(SC)nc3N=C2N)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 2f945347918bf28723fcf5428dd0ab9c21a0ce1ca84ababe9e1f2729326fd176 | b57bdbe728a8b92000f0fde9e9afe3b122c54cb15f189300cc8bbbea277457ba | C1=Nc2ncncc2CN1c1ccccc1 | Br-[C;H0;D2;+0:1]#[N;H0;D1;+0:2].[NH2;D1;+0:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1-[C:10]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[NH2;D1;+0:2]-[C;H0;D3;+0:1]1=[N;H0;D2;+0:3]-[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:2-[C:10]-[N;H0;D3;+0:11]-1-[c:12](:[c:13]):[c:14] | 27.1 | [{"value": 24.0, "product": "COC=1C=C(C=C(C1)OC)N1C(=NC2=NC(=NC=C2C1)SC)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.1, "product": "COC=1C=C(C=C(C1)OC)N1C(=NC2=NC(=NC=C2C1)SC)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a solution of 25.0 g (81.6 mmol) of 5-[(3,5-dimethoxy-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-ylamine in 125 mL of dry dimethylformamide cooled to 5° C., was added a solution of 10.1 g (95.5 mmol) of cyanogen bromide in 25 mL of dry dimethylformamide portionwise. After the addition of the cyanogen bromid... | 10.6084/m9.figshare.5104873.v1 | null | Haloalkyne.Nitrile.Primary amine.Secondary amine | Primary amine.Tertiary amine | null | C1=Nc2ncncc2C[NH]1 | c1ccccc1.C1=Nc2ncncc2C[NH]1 | HBr | CN(C=O)C | null | null | COc1cc(NCc2cnc(SC)nc2N)cc(OC)c1.N#CBr>CN(C=O)C>COc1cc(OC)cc(N2Cc3cnc(SC)nc3N=C2N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8873e0a4b3a2442eba1a48d62786bdc7 | CC(C)N.CCOC(=O)c1cnc(SC)nc1Cl>>CCOC(=O)c1cnc(SC)nc1NC(C)C | ClC1=NC(=NC=C1C(=O)OCC)SC.C(C)N(CC)CC.C(C)(C)N>>C(C)(C)NC1=NC(=NC=C1C(=O)OCC)SC | [NH2:14][CH:15]([CH3:16])[CH3:17].Cl[c:13]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][c:9]([S:10][CH3:11])[n:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([S:10][CH3:11])[n:12][c:13]1[NH:14][CH:15]([CH3:16])[CH3:17] | CC(C)N.CCOC(=O)c1cnc(SC)nc1Cl | CCOC(=O)c1cnc(SC)nc1NC(C)C | null | null | ClCCl.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C;D1;H3:12]-[C:13](-[C;D1;H3:14])-[NH2;D1;+0:15]>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:15]-[C:13](-[C;D1;H3:12])-[C;D1;H3:14]):[c:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]):[c:6]:[#7;a:5]:1 | null | [] | 0 | CELSIUS | 2 | HOUR | To a 0° C. solution of 10.0 g (43.0 mmol) of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate and 7.2 mL (51.6 mmol) of triethylamine in 100 mL of dichloromethane is added 4.4 mL (51.6 mmol) of isopropylamine. The reaction solution is stirred at 0° C. for 2 hours then allowed to warm to room temperature. The react... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | ClCCl.C(C)(=O)OCC | 0 | 2 | CC(C)N.CCOC(=O)c1cnc(SC)nc1Cl>ClCCl.C(C)(=O)OCC>CCOC(=O)c1cnc(SC)nc1NC(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe62e3f1d3e445e1a47193d0675cf0e7 | CCOC(=O)c1cnc(SC)nc1NC(C)C>>CSc1ncc(C(=O)O)c(NC(C)C)n1 | C(C)(C)NC1=NC(=NC=C1C(=O)OCC)SC.[OH-].[Na+]>>C(C)(C)NC1=NC(=NC=C1C(=O)O)SC | CC[O:9][C:7]([c:6]1[cH:5][n:4][c:3]([S:2][CH3:1])[n:15][c:10]1[NH:11][CH:12]([CH3:13])[CH3:14])=[O:8]>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]([NH:11][CH:12]([CH3:13])[CH3:14])[n:15]1 | CCOC(=O)c1cnc(SC)nc1NC(C)C | CSc1ncc(C(=O)O)c(NC(C)C)n1 | null | null | O.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cncnc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[c:5]:[#7;a:6]):[c:7]:[#7;a:8]>>[#7;a:6]:[c:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:7]:[#7;a:8] | 90 | [{"value": 90.0, "product": "C(C)(C)NC1=NC(=NC=C1C(=O)O)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.8, "product": "C(C)(C)NC1=NC(=NC=C1C(=O)O)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 5.0 g (19.6 mmol) of ethyl 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylate in 20 mL of ethanol is added a solution of 0.8 g (20.6 mmol) of sodium hydroxide in 30 mL of water. The reaction suspension is stirred at room temperature overnight. The reaction solution is diluted with 100 mL of wate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1 | Other | O.C(C)O | null | 8 | CCOC(=O)c1cnc(SC)nc1NC(C)C>O.C(C)O>CSc1ncc(C(=O)O)c(NC(C)C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b250297335942b299c47a4902d0c23c | CSc1ncc(C(=O)O)c(NC(C)C)n1.O=S(Cl)Cl>>CSc1ncc(C(=O)Cl)c(NC(C)C)n1 | C(C)(C)NC1=NC(=NC=C1C(=O)O)SC.S(=O)(Cl)Cl>>C(C)(C)NC1=NC(=NC=C1C(=O)Cl)SC | O[C:7]([c:6]1[cH:5][n:4][c:3]([S:2][CH3:1])[n:15][c:10]1[NH:11][CH:12]([CH3:13])[CH3:14])=[O:8].O=S(Cl)[Cl:9]>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[Cl:9])[c:10]([NH:11][CH:12]([CH3:13])[CH3:14])[n:15]1 | CSc1ncc(C(=O)O)c(NC(C)C)n1.O=S(Cl)Cl | CSc1ncc(C(=O)Cl)c(NC(C)C)n1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1cncnc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c: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:5]:[c:4]:1-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 50 | CELSIUS | null | null | To 3.5 (15.4 mmol) of 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic acid is added 9.0 mL (123.2 mmol) of thionyl chloride, and the reaction mixture is heated at 50° C. for 1 hour, cooled to room temperature, and concentrated. The residue is twice suspended in anhydrous toluene and concentrated to give a colo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1cncnc1 | HCl | null | 50 | null | CSc1ncc(C(=O)O)c(NC(C)C)n1.O=S(Cl)Cl>>CSc1ncc(C(=O)Cl)c(NC(C)C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-161ff308cde042ffb55afce2d51f1f15 | C=CCN.CSc1ncc(C(=O)Cl)c(NC(C)C)n1>>C=CCNC(=O)c1cnc(SC)nc1NC(C)C | C(C)(C)NC1=NC(=NC=C1C(=O)Cl)SC.C(C=C)N>>C(C=C)NC(=O)C=1C(=NC(=NC1)SC)NC(C)C | [CH2:1]=[CH:2][CH2:3][NH2:4].Cl[C:5](=[O:6])[c:7]1[cH:8][n:9][c:10]([S:11][CH3:12])[n:13][c:14]1[NH:15][CH:16]([CH3:17])[CH3:18]>>[CH2:1]=[CH:2][CH2:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][n:9][c:10]([S:11][CH3:12])[n:13][c:14]1[NH:15][CH:16]([CH3:17])[CH3:18] | C=CCN.CSc1ncc(C(=O)Cl)c(NC(C)C)n1 | C=CCNC(=O)c1cnc(SC)nc1NC(C)C | null | null | O1CCCC1.C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cncnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[#7:9].[C;D1;H2:10]=[C:11]-[C:12]-[NH2;D1;+0:13]>>[#7:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:[c:3]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C:12]-[C:11]=[C;D1;H2:10] | 51 | [{"value": 51.0, "product": "C(C=C)NC(=O)C=1C(=NC(=NC1)SC)NC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a 0° C. suspension of 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic acid chloride in 10 mL of tetrahydrofuran is added 3.5 mL (46.2 mmol) of allylamine and 20 mL of tetrahydrofuran. The reaction suspension is allowed to warm briefly to room temperature, then stored at 0° C. overnight. The reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cncnc1 | HCl | O1CCCC1.C(C)(=O)OCC | null | 8 | C=CCN.CSc1ncc(C(=O)Cl)c(NC(C)C)n1>O1CCCC1.C(C)(=O)OCC>C=CCNC(=O)c1cnc(SC)nc1NC(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-07636a58e7fc418da226ad5ecd156cb1 | COc1ccc(CN)cc1.CSc1ncc(C(=O)Cl)c(NC(C)C)n1>>COc1ccc(CNC(=O)c2cnc(SC)nc2NC(C)C)cc1 | C(C)(C)NC1=NC(=NC=C1C(=O)Cl)SC.COC1=CC=C(CN)C=C1>>COC1=CC=C(CNC(=O)C=2C(=NC(=NC2)SC)NC(C)C)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:23][cH:24]1.Cl[C:9](=[O:10])[c:11]1[cH:12][n:13][c:14]([S:15][CH3:16])[n:17][c:18]1[NH:19][CH:20]([CH3:21])[CH3:22]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][C:9](=[O:10])[c:11]2[cH:12][n:13][c:14]([S:15][CH3:16])[n:17][c:18]2[NH:19][CH:20]([CH3:21])[CH3:2... | COc1ccc(CN)cc1.CSc1ncc(C(=O)Cl)c(NC(C)C)n1 | COc1ccc(CNC(=O)c2cnc(SC)nc2NC(C)C)cc1 | null | null | ClCCl.O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1ccccc1)c1cncnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[#7:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[#7:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:[c:3]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:11]-[c:12] | 61 | [{"value": 61.0, "product": "COC1=CC=C(CNC(=O)C=2C(=NC(=NC2)SC)NC(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a 0° C. suspension of 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic acid chloride (as prepared in the above example, Preparation 16) in 30 mL of tetrahydrofuran is added 6.0 mL (46.3 mmol) of 4-methoxybenzylamine and 30 mL of tetrahydrofuran. The reaction suspension is allowed to warm briefly to room temp... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1cncnc1 | HCl | ClCCl.O1CCCC1 | null | 8 | COc1ccc(CN)cc1.CSc1ncc(C(=O)Cl)c(NC(C)C)n1>ClCCl.O1CCCC1>COc1ccc(CNC(=O)c2cnc(SC)nc2NC(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac754ce802eb4a8fb1ff30297704f267 | C=CCn1c(=O)c2cnc(-n3ccnc3)nc2n(C(C)C)c1=O.CN1CCN(c2ccc(N)cc2)CC1>>C=CCn1c(=O)c2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc2n(C(C)C)c1=O | C(C=C)N1C(N(C2=NC(=NC=C2C1=O)N1C=NC=C1)C(C)C)=O.NC1=CC=C(C=C1)N1CCN(CC1)C>>C(C=C)N1C(N(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1CCN(CC1)C)C(C)C)=O | c1cn(-[c:10]2[n:9][cH:8][c:7]3[c:5](=[O:6])[n:4]([CH2:3][CH:2]=[CH2:1])[c:31](=[O:32])[n:27]([CH:28]([CH3:29])[CH3:30])[c:26]3[n:25]2)cn1.[NH2:11][c:12]1[cH:13][cH:14][c:15]([N:16]2[CH2:17][CH2:18][N:19]([CH3:20])[CH2:21][CH2:22]2)[cH:23][cH:24]1>>[CH2:1]=[CH:2][CH2:3][n:4]1[c:5](=[O:6])[c:7]2[cH:8][n:9][c:10]([NH:11][... | C=CCn1c(=O)c2cnc(-n3ccnc3)nc2n(C(C)C)c1=O.CN1CCN(c2ccc(N)cc2)CC1 | C=CCn1c(=O)c2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc2n(C(C)C)c1=O | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 1bd48639de7c20bf0b5cea2c047532d0b68478f239a233f9b9397f996acf82d1 | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | O=c1[nH]c(=O)c2cnc(Nc3ccc(N4CCNCC4)cc3)nc2[nH]1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]2:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-n3:c:c:n:c:3):[#7;a:10]:[c:11]:1:2.[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]2:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]):[#7;a:10]:[c:11]:1:2 | 60 | [{"value": 60.0, "product": "C(C=C)N1C(N(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1CCN(CC1)C)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.0, "product": "C(C=C)N1C(N(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)N1CCN(CC1)C)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | A mixture of 300 mg (0.96 mmol) of 3-allyl-7-(imidazol-1-yl)-1-isopropyl-1H-pyrimido[4,5-d]pyrimidine-2,4-dione and 551 mg (2.88 mmol) of 1-(4-aminophenyl)-4-methylpiperazine is heated at 180° C. for 2 hours. The reaction mixture is cooled, dissolved into chloroform, and chromatographed on silica eluting with 4:96 meth... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | c1c[nH]cn1.c1ncc2cncnc2n1 | c1ncc2cncnc2n1 | c1ncc2cncnc2n1.c1ccccc1.C1C[NH]CC[NH]1 | Other | C(Cl)(Cl)Cl | 180 | null | C=CCn1c(=O)c2cnc(-n3ccnc3)nc2n(C(C)C)c1=O.CN1CCN(c2ccc(N)cc2)CC1>C(Cl)(Cl)Cl>C=CCn1c(=O)c2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc2n(C(C)C)c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b96d09cd187441369c1609548b040540 | CN1CCN(c2ccc(N)cc2)CC1.COc1ccc(Cn2c(=O)c3cnc(-n4ccnc4)nc3n(C(C)C)c2=O)cc1>>COc1ccc(Cn2c(=O)c3cnc(Nc4ccc(N5CCN(C)CC5)cc4)nc3n(C(C)C)c2=O)cc1 | N1(C=NC=C1)C1=NC=C2C(=N1)N(C(N(C2=O)CC2=CC=C(C=C2)OC)=O)C(C)C.NC1=CC=C(C=C1)N1CCN(CC1)C>>C(C)(C)N1C(N(C(C=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O)CC2=CC=C(C=C2)OC)=O | [NH2:15][c:16]1[cH:17][cH:18][c:19]([N:20]2[CH2:21][CH2:22][N:23]([CH3:24])[CH2:25][CH2:26]2)[cH:27][cH:28]1.c1cn(-[c:14]2[n:13][cH:12][c:11]3[c:9](=[O:10])[n:8]([CH2:7][c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:38][cH:37]4)[c:35](=[O:36])[n:31]([CH:32]([CH3:33])[CH3:34])[c:30]3[n:29]2)cn1>>[CH3:1][O:2][c:3]1[cH:4][cH:5]... | CN1CCN(c2ccc(N)cc2)CC1.COc1ccc(Cn2c(=O)c3cnc(-n4ccnc4)nc3n(C(C)C)c2=O)cc1 | COc1ccc(Cn2c(=O)c3cnc(Nc4ccc(N5CCN(C)CC5)cc4)nc3n(C(C)C)c2=O)cc1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 1bd48639de7c20bf0b5cea2c047532d0b68478f239a233f9b9397f996acf82d1 | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | O=c1[nH]c2nc(Nc3ccc(N4CCNCC4)cc3)ncc2c(=O)n1Cc1ccccc1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]2:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-n3:c:c:n:c:3):[#7;a:10]:[c:11]:1:2.[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]2:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]):[#7;a:10]:[c:11]:1:2 | 58 | [{"value": 58.0, "product": "C(C)(C)N1C(N(C(C=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O)CC2=CC=C(C=C2)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.7, "product": "C(C)(C)N1C(N(C(C=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O)CC2=CC=C(C=C2)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | 180 | CELSIUS | null | null | A mixture of 700 mg (1.78 mmol) of 7-(imidazol-1-yl)-1-isopropyl-3-(4-methoxybenzyl)-1H-pyrimido[4,5-d]pyrimidine-2,4-dione and 1.02 g (5.35 mmol) of 1-(4-aminophenyl)-4-methylpiperazine is heated at 180° C. for 2 hours. The reaction mixture is cooled, dissolved into chloroform, and chromatographed on silica eluting wi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | c1c[nH]cn1.c1ncc2cncnc2n1 | c1ncc2cncnc2n1 | c1ccccc1.c1ncc2cncnc2n1.c1ccccc1.C1C[NH]CC[NH]1 | Other | C(Cl)(Cl)Cl | 180 | null | CN1CCN(c2ccc(N)cc2)CC1.COc1ccc(Cn2c(=O)c3cnc(-n4ccnc4)nc3n(C(C)C)c2=O)cc1>C(Cl)(Cl)Cl>COc1ccc(Cn2c(=O)c3cnc(Nc4ccc(N5CCN(C)CC5)cc4)nc3n(C(C)C)c2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6f2ebe804dea4f879cae4969f796df40 | C=CCn1c(=O)c2cnc(-n3ccnc3)nc2n(C(C)C)c1=O.CCN(CC)CCOc1ccc(N)cc1>>C=CCn1c(=O)c2cnc(Nc3ccc(OCCN(CC)CC)cc3)nc2n(C(C)C)c1=O | C(C=C)N1C(N(C2=NC(=NC=C2C1=O)N1C=NC=C1)C(C)C)=O.C(C)N(CCOC1=CC=C(N)C=C1)CC>>C(C=C)N1C(N(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)OCCN(CC)CC)C(C)C)=O | c1cn(-[c:10]2[n:9][cH:8][c:7]3[c:5](=[O:6])[n:4]([CH2:3][CH:2]=[CH2:1])[c:32](=[O:33])[n:28]([CH:29]([CH3:30])[CH3:31])[c:27]3[n:26]2)cn1.[NH2:11][c:12]1[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][N:19]([CH2:20][CH3:21])[CH2:22][CH3:23])[cH:24][cH:25]1>>[CH2:1]=[CH:2][CH2:3][n:4]1[c:5](=[O:6])[c:7]2[cH:8][n:9][c:10]([N... | C=CCn1c(=O)c2cnc(-n3ccnc3)nc2n(C(C)C)c1=O.CCN(CC)CCOc1ccc(N)cc1 | C=CCn1c(=O)c2cnc(Nc3ccc(OCCN(CC)CC)cc3)nc2n(C(C)C)c1=O | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 1bd48639de7c20bf0b5cea2c047532d0b68478f239a233f9b9397f996acf82d1 | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | O=c1[nH]c(=O)c2cnc(Nc3ccccc3)nc2[nH]1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]2:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-n3:c:c:n:c:3):[#7;a:10]:[c:11]:1:2.[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]2:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]):[#7;a:10]:[c:11]:1:2 | 36.6 | [{"value": 36.0, "product": "C(C=C)N1C(N(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)OCCN(CC)CC)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.6, "product": "C(C=C)N1C(N(C2=NC(=NC=C2C1=O)NC1=CC=C(C=C1)OCCN(CC)CC)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | A mixture of 200 mg (0.64 mmol) of 3-allyl-7-(imidazol-1-yl)-1-isopropyl-1H-pyrimido[4,5-d]pyrimidine-2,4-dione and 400 mg (1.92 mmol) of 4-(2-diethylaminoethoxy)aniline is heated at 180° C. for 3 hours. The reaction mixture is cooled, dissolved into chloroform, and chromatographed on silica eluting with 4:96 methanol/... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | c1c[nH]cn1.c1ncc2cncnc2n1 | c1ncc2cncnc2n1 | c1ncc2cncnc2n1.c1ccccc1 | Other | C(Cl)(Cl)Cl | 180 | null | C=CCn1c(=O)c2cnc(-n3ccnc3)nc2n(C(C)C)c1=O.CCN(CC)CCOc1ccc(N)cc1>C(Cl)(Cl)Cl>C=CCn1c(=O)c2cnc(Nc3ccc(OCCN(CC)CC)cc3)nc2n(C(C)C)c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d1bd65c1cad471aaf49b4c5d19295ec | CCN(CC)CCOc1ccc(N)cc1.COc1ccc(Cn2c(=O)c3cnc(-n4ccnc4)nc3n(C(C)C)c2=O)cc1>>CCN(CC)CCOc1ccc(Nc2ncc3c(=O)n(Cc4ccc(OC)cc4)c(=O)n(C(C)C)c3n2)cc1 | C1(CCC(=O)O1)=O.CN(C=O)C.N1(C=NC=C1)C1=NC=C2C(=N1)N(C(N(C2=O)CC2=CC=C(C=C2)OC)=O)C(C)C.C(C)N(CCOC1=CC=C(N)C=C1)CC>>C(C)N(CCOC1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(N(C2=O)CC2=CC=C(C=C2)OC)=O)C(C)C)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:38][cH:39]1.c1cn(-[c:14]2[n:15][cH:16][c:17]3[c:18](=[O:19])[n:20]([CH2:21][c:22]4[cH:23][cH:24][c:25]([O:26][CH3:27])[cH:28][cH:29]4)[c:30](=[O:31])[n:32]([CH:33]([CH3:34])[CH3:35])[c:36]3[n:37]2)cn1>>[CH3:1][CH2:2][N:3]([CH2... | CCN(CC)CCOc1ccc(N)cc1.COc1ccc(Cn2c(=O)c3cnc(-n4ccnc4)nc3n(C(C)C)c2=O)cc1 | CCN(CC)CCOc1ccc(Nc2ncc3c(=O)n(Cc4ccc(OC)cc4)c(=O)n(C(C)C)c3n2)cc1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 1bd48639de7c20bf0b5cea2c047532d0b68478f239a233f9b9397f996acf82d1 | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | O=c1[nH]c2nc(Nc3ccccc3)ncc2c(=O)n1Cc1ccccc1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]2:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-n3:c:c:n:c:3):[#7;a:10]:[c:11]:1:2.[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6]2:[c:7]:[#7;a:8]:[c;H0;D3;+0:9](-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]):[#7;a:10]:[c:11]:1:2 | 62.2 | [{"value": 61.0, "product": "C(C)N(CCOC1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(N(C2=O)CC2=CC=C(C=C2)OC)=O)C(C)C)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.2, "product": "C(C)N(CCOC1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(N(C2=O)CC2=CC=C(C=C2)OC)=O)C(C)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | 180 | CELSIUS | null | null | A mixture of 700 mg (1.78 mmol) of 7-(imidazol-1-yl)-1-isopropyl-3-(4-methoxybenzyl)-1H-pyrimido[4,5-d]pyrimidine-2,4-dione and 1.1 g (5.35 mmol) of 4-(2-diethylaminoethoxy)aniline is heated at 180° C. for 4 hours, then cooled. To the reaction mixture is added 357 mg (3.6 mmol) of succinic anhydride, 1 mL of chloroform... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | c1c[nH]cn1.c1ncc2cncnc2n1 | c1ncc2cncnc2n1 | c1ccccc1.c1ncc2cncnc2n1.c1ccccc1 | Other | C(Cl)(Cl)Cl | 180 | null | CCN(CC)CCOc1ccc(N)cc1.COc1ccc(Cn2c(=O)c3cnc(-n4ccnc4)nc3n(C(C)C)c2=O)cc1>C(Cl)(Cl)Cl>CCN(CC)CCOc1ccc(Nc2ncc3c(=O)n(Cc4ccc(OC)cc4)c(=O)n(C(C)C)c3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d1705d2162742edbd673f8931227ff9 | FC(F)(F)C1CN(Cc2ccccc2)CCN1Cc1ccccc1>>FC(F)(F)C1CN(Cc2ccccc2)CCN1Cc1ccccc1.FC(F)(F)C1CNCCN1 | C(C1=CC=CC=C1)N1C(CN(CC1)CC1=CC=CC=C1)C(F)(F)F.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C(C1=CC=CC=C1)N1CC(N(CC1)CC1=CC=CC=C1)C(F)(F)F.FC(C1NCCNC1)(F)F | [F:1][C:2]([CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][CH2:16][N:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)([F:25])[F:28]>>[F:1][C:2]([F:3])([F:4])[CH:5]1[CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][CH2:16][N:17]1[CH2:18][c:19]1[cH:20][cH:21][c... | FC(F)(F)C1CN(Cc2ccccc2)CCN1Cc1ccccc1 | FC(F)(F)C1CN(Cc2ccccc2)CCN1Cc1ccccc1.FC(F)(F)C1CNCCN1 | null | null | CC(=O)O | Functional Group Addition | OtherReaction | b012eac0c12a42e1b51ea2b984b09ba4b20cd372d10e0b78c95e5cdd8dc2807a | 2e995d111a89f8869b46de0ada38a2beac5e48dce45770df0e7fa0a68708c8f7 | C1CNCCN1.c1ccc(CN2CCN(Cc3ccccc3)CC2)cc1 | [#7:1]-[C:2]-[C:3](-[C;H0;D4;+0:4](-[F;D1;H0:5])(-[F;H0;D1;+0:6])-[F;H0;D1;+0:7])-[#7:8](-[C:9])-[C:10]>>[#7:1]-[C:2]-[C:3](-[C;H0;D4;+0:4](-[F;D1;H0:5])(-[F;D1;H0:11])-[F;D1;H0:12])-[#7:8](-[C:9])-[C:10].[C:13]-[C:14](-[F;D1;H0:15])(-[F;H0;D1;+0:6])-[F;H0;D1;+0:7] | null | [] | null | null | null | null | 2-Trifluoromethylpiperazine (Jenneskens et al., Ref 88c) was prepared through a four step route (Scheme 56). Using Lewis acid TiCl4, N,N′-dibenzylethylenediamine reacted with trifluoropyruvates to afford the hemiacetal, which was reduced at room temperature by Et3SiH in TFA to afford the lactam. LiAlH4 treatment then r... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group | Trifluoro group.Trifluoro group.Secondary amine.Secondary amine | null | C1CNCCN1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.C1CNCCN1 | Other | CC(=O)O | null | null | FC(F)(F)C1CN(Cc2ccccc2)CCN1Cc1ccccc1>CC(=O)O>FC(F)(F)C1CN(Cc2ccccc2)CCN1Cc1ccccc1.FC(F)(F)C1CNCCN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c15a0fc3022745769c1e4a82e9d2b72d | C1CNCCN1.COC(=O)c1ccccc1>>O=C(c1ccccc1)N1CCNCC1 | N1CCNCC1.C(C1=CC=CC=C1)(=O)OC>>C(C1=CC=CC=C1)(=O)N1CCNCC1 | [NH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1.CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1 | C1CNCCN1.COC(=O)c1ccccc1 | O=C(c1ccccc1)N1CCNCC1 | null | null | C(Cl)Cl | Acylation | Aminolysis of esters | 28fa86b96af5740128c30d4dea8abf89e5ff48bf24970582cfb131225bda0ca7 | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | O=C(c1ccccc1)N1CCNCC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Mono-benzoylation of unsymmetric substituted piperazines could be achieved by using one of the following procedures (Scheme 57), in which all the methods were exemplified by mono-alkyl substituted piperazines. (a) Unsymmetric piperazines were treated with 2 equivalents of n-butyllithium, followed by the addition of ben... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1CNCCN1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HO- | C(Cl)Cl | null | null | C1CNCCN1.COC(=O)c1ccccc1>C(Cl)Cl>O=C(c1ccccc1)N1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc11b96e28234686b2ec9011cf6fff2e | COc1ccc(N)cn1.Oc1ccc(F)cn1>>COc1ncccc1F | OC1=NC=C(C=C1)F.NC=1C=CC(=NC1)OC.OC1=NC=C(C=C1[N+](=O)[O-])F>>COC1=NC=CC=C1F | N[c:6]1cc[c:3]([O:2][CH3:1])[n:4][cH:5]1.Oc1c[cH:7][c:8]([F:9])cn1>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[F:9] | COc1ccc(N)cn1.Oc1ccc(F)cn1 | COc1ncccc1F | null | null | null | Miscellaneous | OtherReaction | d6c642119818c9dbf58e9ef364fc8a65264d44275d52775a77245ea74936f5b2 | 91d2628360d07d0418a137792f7c1c94d1ef520f09f514e22d9efcbfc02fd8f6 | c1ccncc1 | N-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c;H0;D3;+0:4](-[#8:5]-[C;D1;H3:6]):c:c:1.O-c1:c:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[F;D1;H0:9]):c:n:1>>[C;D1;H3:6]-[#8:5]-[c;H0;D3;+0:4]1:[#7;a:3]:[c:2]:[cH;D2;+0:1]:[cH;D2;+0:7]:[c;H0;D3;+0:8]:1-[F;D1;H0:9] | null | [] | null | null | null | null | Scheme 80 is a preferred method for making compounds of Formula I and Ia where R2 is fluoro. This is exemplified specifically in the preparation of compound Example 216. The synthesis of 2-hydroxy-3-nitro-5-fluoropyridine 5-80 as shown was carried out generally via the methods of A. Marfat and R. P. Robinson U.S. Pat. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Aromatic alcohol.Primary amine | Aromatic halide.Ether | c1ccncc1.c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | null | null | null | COc1ccc(N)cn1.Oc1ccc(F)cn1>>COc1ncccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ebd7f08b85174793a90ed0cc6a1ebd13 | O=[N+]([O-])c1cc(F)cnc1Br.O=[N+]([O-])c1cc(F)cnc1O>>Fc1cnc(Br)c2[nH]ccc12 | P(=O)(Br)(Br)Br.OC1=NC=C(C=C1[N+](=O)[O-])F.BrC1=NC=C(C=C1[N+](=O)[O-])F>>FC1=C2C=CNC2=C(N=C1)Br | O=[N+:8]([O-])[c:7]1[c:5]([Br:6])[n:4][cH:3][c:2]([F:1])[cH:11]1.O=[N+]([O-])c1c(O)nc[c:9](F)[cH:10]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Br:6])[c:7]2[nH:8][cH:9][cH:10][c:11]12 | O=[N+]([O-])c1cc(F)cnc1Br.O=[N+]([O-])c1cc(F)cnc1O | Fc1cnc(Br)c2[nH]ccc12 | null | null | null | Functional Group Interconversion | OtherReaction | bfffef3aed9565a89ab8b357171ae6fc07599b8d7168855cd83e0a6f5968bc8e | f927da59b29d36cbe8e58d89120fe0fa3d8a6a3d9c2a2e0f4e2fcf5c01966e5f | c1cc2cc[nH]c2cn1 | F-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:c(-[N+](=O)-[O-]):c(-O):n:c:1.O=[N+;H0;D3:3](-[O-])-[c:4]1:[cH;D2;+0:5]:[c:6](-[F;D1;H0:7]):[c:8]:[#7;a:9]:[c:10]:1-[Br;D1;H0:11]>>[Br;D1;H0:11]-[c:10]1:[#7;a:9]:[c:8]:[c:6](-[F;D1;H0:7]):[c;H0;D3;+0:5]2:[cH;D2;+0:2]:[cH;D2;+0:1]:[nH;D2;+0:3]:[c:4]:1:2 | null | [] | null | null | null | null | Scheme 80 is a preferred method for making compounds of Formula I and Ia where R2 is fluoro. This is exemplified specifically in the preparation of compound Example 216. The synthesis of 2-hydroxy-3-nitro-5-fluoropyridine 5-80 as shown was carried out generally via the methods of A. Marfat and R. P. Robinson U.S. Pat. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group.Nitro group.Aromatic alcohol | null | c1ccncc1.c1ccncc1 | c1cc2cc[nH]c2cn1 | c1cc2cc[nH]c2cn1 | HF | null | null | null | O=[N+]([O-])c1cc(F)cnc1Br.O=[N+]([O-])c1cc(F)cnc1O>>Fc1cnc(Br)c2[nH]ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96b057b00586404b97355a27251e06af | COc1ccc(B(O)O)cc1.O=[N+]([O-])c1cnccc1Cl>>COc1ccc(-c2ccncc2[N+](=O)[O-])cc1 | COC1=CC=C(C=C1)B(O)O.Cl.ClC1=C(C=NC=C1)[N+](=O)[O-].C(=O)([O-])[O-].[K+].[K+]>>[N+](=O)([O-])C=1C=NC=CC1C1=CC=C(C=C1)OC | OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:17][cH:16]1.Cl[c:7]1[cH:8][cH:9][n:10][cH:11][c:12]1[N+:13](=[O:14])[O-:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][c:12]2[N+:13](=[O:14])[O-:15])[cH:16][cH:17]1 | COc1ccc(B(O)O)cc1.O=[N+]([O-])c1cnccc1Cl | COc1ccc(-c2ccncc2[N+](=O)[O-])cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[#7;+:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;+:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12] | null | [] | null | null | null | null | 4-Methoxyphenylboronic acid (24.54 g), 4-chloro-3-nitropyridine hydrochloride (26.24 g), Pd(Ph3P)4 (4 g) and K2CO3 (111 g) were combined in DME (500 mL). The reaction was heated to reflux for 10 hours. After the mixture cooled down to room temperature, it was poured into saturated aqueous NH4OAc (500 mL) solution. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HCl.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC | null | null | COc1ccc(B(O)O)cc1.O=[N+]([O-])c1cnccc1Cl>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC>COc1ccc(-c2ccncc2[N+](=O)[O-])cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-21b9013259e34bfeae68c6ae96ec5f1e | C[O-].Clc1ncc(Br)c2cc[nH]c12>>COc1cnc(Cl)c2[nH]ccc12 | BrC1=C2C=CNC2=C(N=C1)Cl.C[O-].[Na+].Cl>>COC1=C2C=CNC2=C(N=C1)Cl | [CH3:1][O-:2].Br[c:3]1[cH:4][n:5][c:6]([Cl:7])[c:8]2[nH:9][cH:10][cH:11][c:12]12>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([Cl:7])[c:8]2[nH:9][cH:10][cH:11][c:12]12 | C[O-].Clc1ncc(Br)c2cc[nH]c12 | COc1cnc(Cl)c2[nH]ccc12 | null | [Cu]I | CO | Heteroatom Alkylation and Arylation | OtherReaction | 40e9d73b5c8f97bee789fca96f74e99a8d511b80c9ca26e7dce8a9ae76b6f12f | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1cc2cc[nH]c2cn1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[c:9]:2:1.[C;D1;H3:10]-[O-;H0;D1:11]>>[C;D1;H3:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[c:9]:2:1 | null | [] | 115 | CELSIUS | null | null | A mixture of 4-bromo-7-chloro-6-azaindole (1 g), CuI (0.65 g) and NaOMe (4 mL, 25% in methanol) in MeOH (16 mL) was heated at 110-120° C. for 16 hours in a sealed tube. After cooling to room temperature, the reaction mixture was neutralized with 1N HCl to pH 7. The aqueous solution was extracted with EtOAc (3×30 mL). T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1cc2cc[nH]c2cn1 | c1cc2cc[nH]c2cn1 | c1cc2cc[nH]c2cn1 | Br- | [Cu]I.CO | 115 | null | C[O-].Clc1ncc(Br)c2cc[nH]c12>[Cu]I.CO>COc1cnc(Cl)c2[nH]ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de5271c0bf804766858a10ffe680bddc | C[O-].Clc1ncc(Br)c2cc[nH]c12>>COc1cnc(Cl)c2[nH]ccc12 | BrC1=C2C=CNC2=C(N=C1)Cl.C[O-].[Na+].[NH4+].[Cl-]>>COC1=C2C=CNC2=C(N=C1)Cl | [CH3:1][O-:2].Br[c:3]1[cH:4][n:5][c:6]([Cl:7])[c:8]2[nH:9][cH:10][cH:11][c:12]12>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([Cl:7])[c:8]2[nH:9][cH:10][cH:11][c:12]12 | C[O-].Clc1ncc(Br)c2cc[nH]c12 | COc1cnc(Cl)c2[nH]ccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 40e9d73b5c8f97bee789fca96f74e99a8d511b80c9ca26e7dce8a9ae76b6f12f | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1cc2cc[nH]c2cn1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[c:9]:2:1.[C;D1;H3:10]-[O-;H0;D1:11]>>[C;D1;H3:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[c:9]:2:1 | null | [] | 110 | CELSIUS | null | null | A mixture of 4-bromo-7-chloro-6-azaindole (6 g), CuBr (3.7 g) and NaOMe (30 mL, 5% in MeOH) was heated at 110° C. for 24 hours in a sealed tube. After cooling to room temperature, the reaction mixture was added to saturated aqueous NH4Cl. The resulting aqueous solution was extracted with EtOAc (3×30 mL). The combined o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1cc2cc[nH]c2cn1 | c1cc2cc[nH]c2cn1 | c1cc2cc[nH]c2cn1 | Br- | null | 110 | null | C[O-].Clc1ncc(Br)c2cc[nH]c12>>COc1cnc(Cl)c2[nH]ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb142696effe437d876e7f0f1047698d | O=[N+]([O-])c1cc(Br)cnc1Cl.c1cn[nH]c1>>O=[N+]([O-])c1cc(Br)cnc1-n1cccn1 | BrC=1C=C(C(=NC1)Cl)[N+](=O)[O-].N1N=CC=C1>>BrC=1C=C(C(=NC1)N1N=CC=C1)[N+](=O)[O-] | Cl[c:10]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][c:6]([Br:7])[cH:8][n:9]1.[nH:11]1[cH:12][cH:13][cH:14][n:15]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Br:7])[cH:8][n:9][c:10]1-[n:11]1[cH:12][cH:13][cH:14][n:15]1 | O=[N+]([O-])c1cc(Br)cnc1Cl.c1cn[nH]c1 | O=[N+]([O-])c1cc(Br)cnc1-n1cccn1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 8c8ea70bdc6e12e9a778ea0491595faafe3ec0c0a7fe7f6ae4184d378f504c00 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2cccn2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[#7;a:7]1:[c:8]:[c:9]:[c:10]:[nH;D2;+0:11]:1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[n;H0;D3;+0:11]1:[#7;a:7]:[c:8]:[c:9]:[c:10]:1):[#7;a:2]:[c:3] | null | [] | 120 | CELSIUS | 26.5 | HOUR | To a mixture of 5-bromo-2-chloro-3-nitropyridine (10 g, 42 mmol) in 1,4-dioxane (100 ml) was added pyrazole (5.8 g, 85 mmol). The resulting mixture was stirred at 120° C. for 26.5 h., and then evaporated after cooling to r.t. The crude material was purified by flash chromatography (0 to 5% EtOAc/Hexanes) to give the de... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1.c1cn[nH]c1 | c1ccncc1.c1cn[nH]c1 | c1ccncc1.c1cn[nH]c1 | HCl | O1CCOCC1 | 120 | 26.5 | O=[N+]([O-])c1cc(Br)cnc1Cl.c1cn[nH]c1>O1CCOCC1>O=[N+]([O-])c1cc(Br)cnc1-n1cccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7b4460955d654769824591632d1f6630 | COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)[O-])c12.O=C(c1ccccc1)N1CCNCC1>>COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | C(C1=CC=CC=C1)(=O)N1CCNCC1.ClC=1N=CC(=C2C(=CNC12)C(C(=O)[O-])=O)OC.[K+]>>C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)Cl)=O | [O-][C:14]([C:12]([c:11]1[cH:10][nH:9][c:8]2[c:6]([Cl:7])[n:5][cH:4][c:3]([O:2][CH3:1])[c:30]21)=[O:13])=[O:15].[NH:16]1[CH2:17][CH2:18][N:19]([C:20](=[O:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([Cl:7])[c:8]2[nH:9][cH:10][c:11]([C:12](=[O:13])[C:14](=[O:15])[... | COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)[O-])c12.O=C(c1ccccc1)N1CCNCC1 | COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2cnccc12 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | Precursor 5b, 1-benzoyl-4-[(7-chloro-4-methoxy-6-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a starting from Potassium (7-chloro-4-methoxy-6-azaindol-3-yl)-oxoacetate, Precursor 4d, and 1-benzoylpiperazine. MS m/z: (M+H)+ calcd for C21H20ClN4O4: 427.12; found 427.12. HPLC retention... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1cc2cc[nH]c2cn1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | null | null | null | COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)[O-])c12.O=C(c1ccccc1)N1CCNCC1>>COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-366bc8e54aa84a60b04042c260ce0c55 | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Cl)ccnc12>>C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2c(Cl)ccnc12 | C(C1=CC=CC=C1)(=O)N1C[C@H](NCC1)C.ClC=1C=CN=C2C(=CNC12)C(C(=O)[O-])=O.[K+]>>C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(C(=O)C1=CNC2=C(C=CN=C12)Cl)=O)C | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][NH:15]1.[O-][C:16](=[O:17])[C:18](=[O:19])[c:20]1[cH:21][nH:22][c:23]2[c:24]([Cl:25])[cH:26][cH:27][n:28][c:29]12>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][N:15]... | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Cl)ccnc12 | C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2c(Cl)ccnc12 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2cccnc12 | [#7;a:1]:[c:2]:[c:3](-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7]):[c:8]:[#7;a:9].[C;D1;H3:10]-[C:11]1-[C:12]-[#7:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[#7;a:1]:[c:2]:[c:3](-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:16]1-[C:15]-[C:14]-[#7:13]-[C:12]-[C:11]-1-[C;D1;H3:10]):[c:8]:[#7;a:9] | null | [] | null | null | null | null | Precursor 5d, 1-benzoyl-3-(R)-methyl-4-[(7-chloro-4-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a, starting from Potassium (7-chloro-4-azaindol-3-yl)-oxoacetate, Precursor 4e, and 1-benzoyl-3-(R)-methyl piperazine. MS m/z: (M+H)+ calcd for C21H20ClN4O3 411.12, found 411.04. HPLC re... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1cnc2cc[nH]c2c1 | HO- | null | null | null | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Cl)ccnc12>>C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2c(Cl)ccnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0d40ebf93bf4947bb0c77ad323c0713 | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.Cc1cc(Cl)nc2c(C(=O)C(=O)[O-])c[nH]c12>>Cc1cc(Cl)nc2c(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)C[C@H]3C)c[nH]c12 | C(C1=CC=CC=C1)(=O)N1C[C@H](NCC1)C.ClC=1N=C2C(=CNC2=C(C1)C)C(C(=O)[O-])=O.[K+]>>C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(C(=O)C1=CNC2=C(C=C(N=C12)Cl)C)=O)C | [NH:13]1[CH2:14][CH2:15][N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25][C@H:26]1[CH3:27].[O-][C:11]([C:9]([c:8]1[c:7]2[n:6][c:4]([Cl:5])[cH:3][c:2]([CH3:1])[c:30]2[nH:29][cH:28]1)=[O:10])=[O:12]>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[n:6][c:7]2[c:8]([C:9](=[O:10])[C:11](=[O:12])[N:13]3[CH2:14][CH2... | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.Cc1cc(Cl)nc2c(C(=O)C(=O)[O-])c[nH]c12 | Cc1cc(Cl)nc2c(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)C[C@H]3C)c[nH]c12 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2cccnc12 | [#7;a:1]:[c:2]:[c:3](-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7]):[c:8]:[#7;a:9].[C;D1;H3:10]-[C:11]1-[C:12]-[#7:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[#7;a:1]:[c:2]:[c:3](-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:16]1-[C:15]-[C:14]-[#7:13]-[C:12]-[C:11]-1-[C;D1;H3:10]):[c:8]:[#7;a:9] | null | [] | null | null | null | null | Precursor 5e, 1-benzoyl-3-(R)-methyl-4-[(5-chloro-7-methyl-4-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a, starting from Potassium (5-chloro-7-methyl-4-azaindol-3-yl)-oxoacetate, Precursor 4f, and 1-benzoyl-3-(R)-methyl piperazine. MS m/z: (M+H)+ calcd for C22H22ClN4O3 425.24, fou... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1cnc2cc[nH]c2c1 | HO- | null | null | null | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.Cc1cc(Cl)nc2c(C(=O)C(=O)[O-])c[nH]c12>>Cc1cc(Cl)nc2c(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)C[C@H]3C)c[nH]c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-52687537d26442759399f73147a374df | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Br)nccc12>>C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2c(Br)nccc12 | C(C1=CC=CC=C1)(=O)N1C[C@H](NCC1)C.[K+].BrC=1N=CC=C2C(=CNC12)C(C(=O)[O-])=O>>C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(C(=O)C1=CNC2=C(N=CC=C12)Br)=O)C | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][NH:15]1.[O-][C:16](=[O:17])[C:18](=[O:19])[c:20]1[cH:21][nH:22][c:23]2[c:24]([Br:25])[n:26][cH:27][cH:28][c:29]12>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][N:15]... | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Br)nccc12 | C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2c(Br)nccc12 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2cnccc12 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7].[C;D1;H3:8]-[C:9]1-[C:10]-[#7:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:10]-[C:9]-1-[C;D1;H3:8] | null | [] | null | null | null | null | Precursor 5f, 1-benzoyl-3-(R)-methyl-4-[(7-bromo-6-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a, starting from (7-bromo-6-azaindol-3-yl)-oxoacetic acid potassium salt, Precursor 4g, and 1-benzoyl-3-(R)-methylpiperazine. MS m/z: (M+H)+ calcd for C21H20BrN4O3: 455.07; found 455.14. ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1cc2cc[nH]c2cn1 | HO- | null | null | null | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Br)nccc12>>C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2c(Br)nccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b20d94ebdbd4a94a4bec7eefc1463df | O=C([O-])C(=O)c1c[nH]c2c(Br)nccc12.O=C(c1ccccc1)N1CCNCC1>>O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Br)nccc12 | C(C1=CC=CC=C1)(=O)N1CCNCC1.[K+].BrC=1N=CC=C2C(=CNC12)C(C(=O)[O-])=O>>C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC=C12)Br)=O | [O-][C:3]([C:2](=[O:1])[c:19]1[cH:20][nH:21][c:22]2[c:23]([Br:24])[n:25][cH:26][cH:27][c:28]12)=[O:4].[NH:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18]1>>[O:1]=[C:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:... | O=C([O-])C(=O)c1c[nH]c2c(Br)nccc12.O=C(c1ccccc1)N1CCNCC1 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Br)nccc12 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2cnccc12 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | Precursor 5g, 1-benzoyl-4-[(7-bromo-6-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a, starting from (7-bromo-6-azaindol-3-yl)-oxoacetic acid potassium salt, Precursor 4g, and 1-benzoylpiperazine. MS m/z: (M+H)+ calcd for C20H18BrN4O3: 441.06; found 441.07. HPLC retention time: 1.43 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1cc2cc[nH]c2cn1 | HO- | null | null | null | O=C([O-])C(=O)c1c[nH]c2c(Br)nccc12.O=C(c1ccccc1)N1CCNCC1>>O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Br)nccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf037c06287b432c9c835d8afecd9068 | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.O=C([O-])C(=O)c1c[nH]c2cnccc12>>C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2cnccc12 | C(C1=CC=CC=C1)(=O)N1C[C@H](NCC1)C.N1C=C(C2=CC=NC=C12)C(C(=O)[O-])=O.[K+]>>C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(C(=O)C1=CNC2=CN=CC=C12)=O)C | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][NH:15]1.[O-][C:16](=[O:17])[C:18](=[O:19])[c:20]1[cH:21][nH:22][c:23]2[cH:24][n:25][cH:26][cH:27][c:28]12>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][N:15]1[C:16](... | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.O=C([O-])C(=O)c1c[nH]c2cnccc12 | C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2cnccc12 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2cnccc12 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7].[C;D1;H3:8]-[C:9]1-[C:10]-[#7:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:10]-[C:9]-1-[C;D1;H3:8] | null | [] | null | null | null | null | Precursor 5h, 1-benzoyl-3-(R)-methyl-4-[(6-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a starting from Potassium (6-azaindol-3-yl)oxoacetate, Precursor 4b, and 1-benzoyl-3-(R)-methylpiperazine. MS m/z: (M+H)+ Calc'd for C21H21N4O3: 377.16; Found 377.10. HPLC retention time: 0.88 mi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1cc2cc[nH]c2cn1 | HO- | null | null | null | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.O=C([O-])C(=O)c1c[nH]c2cnccc12>>C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2cnccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2d13c811ae51411195154d5640ba11cb | O=C([O-])C(=O)c1c[nH]c2c(Cl)ncc(F)c12.O=C(c1ccccc1)N1CCNCC1>>O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Cl)ncc(F)c12 | ClC=1N=CC(=C2C(=CNC12)C(C(=O)[O-])=O)F.[K+].C(C1=CC=CC=C1)(=O)N1CCNCC1.CCOP(=O)(OCC)ON1C(=O)C2=C(C=CC=C2)N=N1>>C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)F)Cl)=O | [O-][C:3]([C:2](=[O:1])[c:19]1[cH:20][nH:21][c:22]2[c:23]([Cl:24])[n:25][cH:26][c:27]([F:28])[c:29]12)=[O:4].[NH:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18]1>>[O:1]=[C:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]... | O=C([O-])C(=O)c1c[nH]c2c(Cl)ncc(F)c12.O=C(c1ccccc1)N1CCNCC1 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Cl)ncc(F)c12 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2cnccc12 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | Addition of precursor 2d to a solution of aluminum trichloride in dichloromethane stirring at ambient temperature followed 30 minutes later with chloromethyl or chloroethyl oxalate (according to the method described for precursor 3a) provides either the methyl or ethyl ester, respectively. Hydrolysis with KOH (as in th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1cc2cc[nH]c2cn1 | HO- | null | null | null | O=C([O-])C(=O)c1c[nH]c2c(Cl)ncc(F)c12.O=C(c1ccccc1)N1CCNCC1>>O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Cl)ncc(F)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3019e452c0645ae8beeb8991dd46dc2 | O=C([O-])C(=O)c1c[nH]c2c(Cl)nccc12.O=C(c1ccccc1)N1CCNCC1>>O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Cl)nccc12 | C(C1=CC=CC=C1)(=O)N1CCNCC1.[K+].ClC=1N=CC=C2C(=CNC12)C(C(=O)[O-])=O>>C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC=C12)Cl)=O | [O-][C:3]([C:2](=[O:1])[c:19]1[cH:20][nH:21][c:22]2[c:23]([Cl:24])[n:25][cH:26][cH:27][c:28]12)=[O:4].[NH:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18]1>>[O:1]=[C:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:... | O=C([O-])C(=O)c1c[nH]c2c(Cl)nccc12.O=C(c1ccccc1)N1CCNCC1 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Cl)nccc12 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2cnccc12 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | Precursor 5k, 1-benzoyl-4-[(7-chloro-6-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a, starting from (7-chloro-6-azaindol-3-yl)-oxoacetic acid potassium salt, Precursor 4a, and 1-benzoylpiperazine. MS m/z: (M+H)+ calcd for C20H18ClN4O3: 397.11; found 396.97. HPLC retention time: 2.3... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1cc2cc[nH]c2cn1 | HO- | null | null | null | O=C([O-])C(=O)c1c[nH]c2c(Cl)nccc12.O=C(c1ccccc1)N1CCNCC1>>O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Cl)nccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cbf0132270344b55903bedda3f4f5b19 | COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)[O-])c12.O=C(c1ccccn1)N1CCNCC1>>COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccn4)CC3)c12 | N1=C(C=CC=C1)C(=O)N1CCNCC1.COC1=C2C(=CNC2=C(N=C1)Cl)C(C(=O)[O-])=O.[K+]>>N1=C(C=CC=C1)C(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)Cl)=O | [O-][C:14]([C:12]([c:11]1[cH:10][nH:9][c:8]2[c:6]([Cl:7])[n:5][cH:4][c:3]([O:2][CH3:1])[c:30]21)=[O:13])=[O:15].[NH:16]1[CH2:17][CH2:18][N:19]([C:20](=[O:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][n:27]2)[CH2:28][CH2:29]1>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([Cl:7])[c:8]2[nH:9][cH:10][c:11]([C:12](=[O:13])[C:14](=[O:15])[N... | COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)[O-])c12.O=C(c1ccccn1)N1CCNCC1 | COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccn4)CC3)c12 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccn2)CC1)c1c[nH]c2cnccc12 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | Precursor 51, 1-picolinoyl-4-[(4-methoxy-7-chloro-6-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a starting from Potassium (4-methoxy-7-chloro-6-azaindol-3-yl)oxoacetate, Precursor 4d, and picolinoyl-piperazine. 1H NMR (500 MHz, DMSO-d6) δ 8.63-7.45 (m, 7H), 3.94 (s, 3H), 3.82-2.50 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1cc2cc[nH]c2cn1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | null | null | null | COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)[O-])c12.O=C(c1ccccn1)N1CCNCC1>>COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccn4)CC3)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3e648b493f9f46f7900d4ca6213d75b7 | C[C@@H]1CN(C(=O)c2ccccn2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Br)nccc12>>C[C@@H]1CN(C(=O)c2ccccn2)CCN1C(=O)C(=O)c1c[nH]c2c(Br)nccc12 | C[C@@H]1CN(CCN1)C(C1=NC=CC=C1)=O.BrC=1N=CC=C2C(=CNC12)C(C(=O)[O-])=O.[K+]>>N1=C(C=CC=C1)C(=O)N1C[C@H](N(CC1)C(C(=O)C1=CNC2=C(N=CC=C12)Br)=O)C | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][n:12]2)[CH2:13][CH2:14][NH:15]1.[O-][C:16](=[O:17])[C:18](=[O:19])[c:20]1[cH:21][nH:22][c:23]2[c:24]([Br:25])[n:26][cH:27][cH:28][c:29]12>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][n:12]2)[CH2:13][CH2:14][N:15]1[... | C[C@@H]1CN(C(=O)c2ccccn2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Br)nccc12 | C[C@@H]1CN(C(=O)c2ccccn2)CCN1C(=O)C(=O)c1c[nH]c2c(Br)nccc12 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccn2)CC1)c1c[nH]c2cnccc12 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7].[C;D1;H3:8]-[C:9]1-[C:10]-[#7:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:10]-[C:9]-1-[C;D1;H3:8] | null | [] | null | null | null | null | Precursor 5m, (R)-1-picolinoyl-3-methyl-4-[(7-bromo-6-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a starting from Potassium (7-bromo-6-azaindol-3-yl)oxoacetate, Precursor 4g, and (R)-3-methyl-1-picolinoyl-piperazine. MS m/z: (M+H)+ Calc'd for C20H19BrN5O3: 456.07; Found 456.11. HPL... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccncc1.c1cc2cc[nH]c2cn1 | HO- | null | null | null | C[C@@H]1CN(C(=O)c2ccccn2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Br)nccc12>>C[C@@H]1CN(C(=O)c2ccccn2)CCN1C(=O)C(=O)c1c[nH]c2c(Br)nccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1eb79520a9784ba1af23dffd3379eb93 | C[C@H]1CN(C(=O)c2ccccn2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Br)nccc12>>C[C@H]1CN(C(=O)c2ccccn2)CCN1C(=O)C(=O)c1c[nH]c2c(Br)nccc12 | C[C@H]1CN(CCN1)C(C1=NC=CC=C1)=O.BrC=1N=CC=C2C(=CNC12)C(C(=O)[O-])=O.[K+]>>N1=C(C=CC=C1)C(=O)N1C[C@@H](N(CC1)C(C(=O)C1=CNC2=C(N=CC=C12)Br)=O)C | [CH3:1][C@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][n:12]2)[CH2:13][CH2:14][NH:15]1.[O-][C:16](=[O:17])[C:18](=[O:19])[c:20]1[cH:21][nH:22][c:23]2[c:24]([Br:25])[n:26][cH:27][cH:28][c:29]12>>[CH3:1][C@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][n:12]2)[CH2:13][CH2:14][N:15]1[C:... | C[C@H]1CN(C(=O)c2ccccn2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Br)nccc12 | C[C@H]1CN(C(=O)c2ccccn2)CCN1C(=O)C(=O)c1c[nH]c2c(Br)nccc12 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccn2)CC1)c1c[nH]c2cnccc12 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7].[C;D1;H3:8]-[C:9]1-[C:10]-[#7:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:10]-[C:9]-1-[C;D1;H3:8] | null | [] | null | null | null | null | Precursor 5n, (S)-1-picolinoyl-3-methyl-4-[(7-bromo-6-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a starting from Potassium (7-bromo-6-azaindol-3-yl)oxoacetate, Precursor 4g, and (S)-3-methyl-1-picolinoyl-piperazine. 1H NMR (500 MHz, CDCl3) δ 8.63-7.36 (m, 7H), 5.02-3.06 (m, 7H), 1... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccncc1.c1cc2cc[nH]c2cn1 | HO- | null | null | null | C[C@H]1CN(C(=O)c2ccccn2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Br)nccc12>>C[C@H]1CN(C(=O)c2ccccn2)CCN1C(=O)C(=O)c1c[nH]c2c(Br)nccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2670d46ed5f94f8285d775264343c7db | C[C@@H]1CN(C(=O)c2ccccn2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Br)ncc(F)c12>>C[C@@H]1CN(C(=O)c2ccccn2)CCN1C(=O)C(=O)c1c[nH]c2c(Br)ncc(F)c12 | C[C@@H]1CN(CCN1)C(C1=NC=CC=C1)=O.BrC=1N=CC(=C2C(=CNC12)C(C(=O)[O-])=O)F.[K+]>>N1=C(C=CC=C1)C(=O)N1C[C@H](N(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)F)Br)=O)C | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][n:12]2)[CH2:13][CH2:14][NH:15]1.[O-][C:16](=[O:17])[C:18](=[O:19])[c:20]1[cH:21][nH:22][c:23]2[c:24]([Br:25])[n:26][cH:27][c:28]([F:29])[c:30]12>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][n:12]2)[CH2:13][CH2:14][... | C[C@@H]1CN(C(=O)c2ccccn2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Br)ncc(F)c12 | C[C@@H]1CN(C(=O)c2ccccn2)CCN1C(=O)C(=O)c1c[nH]c2c(Br)ncc(F)c12 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccn2)CC1)c1c[nH]c2cnccc12 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7].[C;D1;H3:8]-[C:9]1-[C:10]-[#7:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:10]-[C:9]-1-[C;D1;H3:8] | null | [] | null | null | null | null | Precursor 5o, (R)-1-picolinoyl-3-methyl-4-[(7-bromo-4-fluoro-6-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a starting from Potassium (7-bromo-4-fluoro-6-azaindol-3-yl)oxoacetate, Precursor 4h, and (R)-3-methyl-1-picolinoyl-piperazine. 1H NMR (500 MHz, CD3OD) δ8.68-7.52 (m, 6H), 4.9... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccncc1.c1cc2cc[nH]c2cn1 | HO- | null | null | null | C[C@@H]1CN(C(=O)c2ccccn2)CCN1.O=C([O-])C(=O)c1c[nH]c2c(Br)ncc(F)c12>>C[C@@H]1CN(C(=O)c2ccccn2)CCN1C(=O)C(=O)c1c[nH]c2c(Br)ncc(F)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a278e3741de400eb1c76860d7c67d07 | O=C([O-])C(=O)c1cnc2c(Cl)ccn(F)c1-2.O=C(c1ccccc1)N1CCNCC1>>O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Cl)ccnc12 | C(C1=CC=CC=C1)(=O)N1CCNCC1.ClC=1C=CN(C2=C(C=NC12)C(C(=O)[O-])=O)F.[K+]>>C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(C=CN=C12)Cl)=O | [O-][C:3]([C:2](=[O:1])[c:19]1[cH:20][n:21][c:22]2[c:23]([Cl:24])[cH:25][cH:26][n:27](F)[c:28]1-2)=[O:4].[NH:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18]1>>[O:1]=[C:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[C... | O=C([O-])C(=O)c1cnc2c(Cl)ccn(F)c1-2.O=C(c1ccccc1)N1CCNCC1 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Cl)ccnc12 | null | null | null | Acylation | OtherReaction | aa708d3f6da9696ecde5f362f208a481a0319e7a3caeb5b3747664278d4f7300 | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2cccnc12 | F-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[Cl;D1;H0:5]):[c;H0;D3;+0:6]2:[n;H0;D2;+0:7]:[c:8]:[c:9](-[C:10](=[O;D1;H0:11])-[C;H0;D3;+0:12](-[O-])=[O;D1;H0:13]):[c;H0;D3;+0:14]:1-2.[#7:15]1-[C:16]-[C:17]-[NH;D2;+0:18]-[C:19]-[C:20]-1>>[Cl;D1;H0:5]-[c:4]1:[c:3]:[c:2]:[n;H0;D2;+0:1]:[c;H0;D3;+0:14]2:[c:9](-[C:10](=[O;D1;H0:11])... | null | [] | null | null | null | null | Precursor 5p, 1-benzoyl-4-[(7-chloro-4-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a starting from Potassium (7-chloro-4-fluoro-4-azaindol-3-yl)oxoacetate, Precursor 4e, and 1-benzoyl-piperazine. 1H NMR (500 MHz, CD3OD) δ8.83 (s, 1H), 8.63 (d, 1H, J=5.35 Hz), 7.91 (d, 1H, J=5.75 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | c1c[nH]c2cccnc12.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1cnc2cc[nH]c2c1 | C1C[NH]CC[NH]1.c1ccccc1.c1cnc2cc[nH]c2c1 | Other | null | null | null | O=C([O-])C(=O)c1cnc2c(Cl)ccn(F)c1-2.O=C(c1ccccc1)N1CCNCC1>>O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Cl)ccnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4d256a9a2454a0eb4e9f3d71bf2ee32 | Brc1ncccn1.CCC[CH2][SnH]([CH2]CCC)[CH2]CCC>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncccn1 | C(CCC)[Sn](CCCC)(CCCC)[Li].C(CCC)[SnH](CCCC)CCCC.[Li+].CC(C)[N-]C(C)C.BrC1=NC=CC=N1>>C(CCC)[Sn](CCCC)(CCCC)[Li].C(CCC)[Sn](C1=NC=CC=N1)(CCCC)CCCC | Br[c:14]1[n:15][cH:16][cH:17][cH:18][n:19]1.[CH3:1][CH2:2][CH2:3][CH2:4][SnH:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[n:15][cH:16][cH:17][cH:18][n:19]1 | Brc1ncccn1.CCC[CH2][SnH]([CH2]CCC)[CH2]CCC | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncccn1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 06ce9e6131574a9a9ec86cf4b8a8e0af94b07d469cfad762bafdbbb9f473a9df | 31a273782785992494eb6bb26e7d587fea5a029768e25f39f813b72e5d926c19 | c1cncnc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[SnH;D3;+0:8](-[C:9]-[C:10])-[C:11]-[C:12]>>[C:6]-[C:7]-[Sn;H0;D4;+0:8](-[C:9]-[C:10])(-[C:11]-[C:12])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | (Example of the general procedure Tin-03, below) Tri-n-butylstannyl lithium was prepared at 0° C. in dry THF (20 mL) from tri-butyltin hydride (2.2 mL) and LDA (lithium diisopropylamide, 2M, 4.09 mL). The tri-n-butylstannyl lithium solution was then cooled to −78° C. and to it was added 2-bromopyrimidine (1 g). The rea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | Tin | c1cncnc1 | c1cncnc1 | c1cncnc1 | HBr | C1CCOC1 | null | null | Brc1ncccn1.CCC[CH2][SnH]([CH2]CCC)[CH2]CCC>C1CCOC1>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1474c4f14abd4bfba50feb262d04b69d | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(N)cn1.CS(=O)(=O)Cl>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(NS(C)(=O)=O)cn1 | [H-].[Na+].NC1=NC=C(N=C1)[Sn](CCCC)(CCCC)CCCC.CS(=O)(=O)Cl>>CS(=O)(=O)NC1=NC=C(N=C1)[Sn](CCCC)(CCCC)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[cH:15][n:16][c:17]([NH2:18])[cH:23][n:24]1.Cl[S:19]([CH3:20])(=[O:21])=[O:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[cH:15][n:16][c:17]([NH:18][S:... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(N)cn1.CS(=O)(=O)Cl | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(NS(C)(=O)=O)cn1 | null | null | C1CCOC1 | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1cnccn1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:[c:11]:1 | 8.3 | [{"value": 8.3, "product": "CS(=O)(=O)NC1=NC=C(N=C1)[Sn](CCCC)(CCCC)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | NaH (60%, 20 mg) was added into a solution of 2-amino-5-(tri-n-butylstannyl)pyrazine (0.2 g) in THF (30 mL) at room temperature. After the mixture stirred at room temperature for 30 minutes, to it was added methylsulfonyl chloride (63 mg). The reaction mixture was stirred at room temperature over 8 hours. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1cnccn1 | HCl | C1CCOC1 | null | 0.5 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(N)cn1.CS(=O)(=O)Cl>C1CCOC1>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(NS(C)(=O)=O)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-972ccdf6e6a24847a0388e9ef7561966 | CC1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2c(Cl)nccc12.OB(O)c1ccc2c(c1)OCO2>>CC1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2c(-c3ccc4c(c3)OCO4)nccc12 | C(C1=CC=CC=C1)(=O)N1CC(N(CC1)C(C(=O)C1=CNC2=C(N=CC=C12)Cl)=O)C.C1OC=2C=C(C=CC2O1)B(O)O>>C(C1=CC=CC=C1)(=O)N1CC(N(CC1)C(C(=O)C1=CNC2=C(N=CC=C12)C1=CC2=C(C=C1)OCO2)=O)C | Cl[c:24]1[c:23]2[nH:22][cH:21][c:20]([C:18]([C:16]([N:15]3[CH:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[c:7]4[cH:8][cH:9][cH:10][cH:11][cH:12]4)[CH2:13][CH2:14]3)=[O:17])=[O:19])[c:37]2[cH:36][cH:35][n:34]1.OB(O)[c:25]1[cH:26][cH:27][c:28]2[c:29]([cH:30]1)[O:31][CH2:32][O:33]2>>[CH3:1][CH:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]... | CC1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2c(Cl)nccc12.OB(O)c1ccc2c(c1)OCO2 | CC1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2c(-c3ccc4c(c3)OCO4)nccc12 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 27731868695eb360ef165511533c82991292ad0336207525cc7deb2597af22f8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(-c3ccc4c(c3)OCO4)nccc12 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]-[#8:13]>>[#8:13]-[c:12]:[c:11]:[c;H0;D3;+0:8](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]):[c:9]:[c:10] | null | [] | null | null | null | null | Example 5, was prepared according to the general method described above from 1-benzoyl-3-methyl-4-[(7-chloro-6-azaindol-3-yl)-oxoacetyl]piperazine and 3,4-methylenedioxyphenyl boronic acid, Precursor 14a-13, to provide 1-benzoyl-3-methyl-4-[(7-(3,4-methylenedioxyphenyl)-6-azaindol-3-yl)-oxoacetyl]piperazine. MS m/z: (M... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2cc[nH]c2cn1.c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.c1cc2cc[nH]c2cn1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)OCO2.c1cc2cc[nH]c2cn1 | HCl.B | null | null | null | CC1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2c(Cl)nccc12.OB(O)c1ccc2c(c1)OCO2>>CC1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2c(-c3ccc4c(c3)OCO4)nccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92dc3f3af6974797bac5c30cff9cfe44 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1.COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)N3CCN(c4ccccn4)CC3)c12>>COc1cnc(-c2nccs2)c2[nH]cc(C(=O)C(=O)N3CCN(c4ccccn4)CC3)c12 | N1=C(C=CC=C1)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)Cl)=O.S1C(=NC=C1)[Sn](CCCC)(CCCC)CCCC>>N1=C(C=CC=C1)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1SC=CN1)=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:7]1[n:8][cH:9][cH:10][s:11]1.Cl[c:6]1[n:5][cH:4][c:3]([O:2][CH3:1])[c:32]2[c:12]1[nH:13][cH:14][c:15]2[C:16](=[O:17])[C:18](=[O:19])[N:20]1[CH2:21][CH2:22][N:23]([c:24]2[cH:25][cH:26][cH:27][cH:28][n:29]2)[CH2:30][CH2:31]1>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6](-[c:7]2[n:8][cH:9][cH:10][... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1.COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)N3CCN(c4ccccn4)CC3)c12 | COc1cnc(-c2nccs2)c2[nH]cc(C(=O)C(=O)N3CCN(c4ccccn4)CC3)c12 | null | null | null | C-C Coupling | Stille reaction_aryl | 652a7a450a9653d69dfd5d8ab996516b303d764225ef315d46f50106b463c832 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=C(C(=O)N1CCN(c2ccccn2)CC1)c1c[nH]c2c(-c3nccs3)nccc12 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.Cl-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[c:9](:[c:10]):[#7;a:11]:[c:12]>>[c:12]:[#7;a:11]:[c:9](:[c:10]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1):[#7;a:7]:[c:8] | null | [] | null | null | null | null | Example 50, was prepared from 1-(pyridin-2-yl)-4-[(4-methoxy-7-chloro-6-azaindol-3-yl)-oxoacetyl]piperazine and thiazol-2-yl tributyltin, Precursor 14a-21, according to the general method above to provide 1-(pyridin-2-yl)-4-[(4-methoxy-7-(thiazol-2-yl)-6-azaindol-3-yl)-oxoacetyl]piperazine MS m/z: (M+H)+ Calc'd for C24... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1cscn1.c1cc2cc[nH]c2cn1 | c1cscn1.c1cc2cc[nH]c2cn1 | c1cscn1.c1cc2cc[nH]c2cn1.C1C[NH]CC[NH]1.c1ccncc1 | HCl.Sn | null | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1.COc1cnc(Cl)c2[nH]cc(C(=O)C(=O)N3CCN(c4ccccn4)CC3)c12>>COc1cnc(-c2nccs2)c2[nH]cc(C(=O)C(=O)N3CCN(c4ccccn4)CC3)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7c329d0c3fb4aa18722a3392f482e91 | COc1cnc(-c2cnc(C(=O)NC(C)(C)C)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12>>COc1cnc(-c2cnc(C(N)=O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1N=CC(=NC1)C(=O)NC(C)(C)C)=O>>C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1N=CC(=NC1)C(=O)N)=O | CC(C)(C)[NH:12][C:11]([c:10]1[n:9][cH:8][c:7](-[c:6]2[n:5][cH:4][c:3]([O:2][CH3:1])[c:38]3[c:16]2[nH:17][cH:18][c:19]3[C:20](=[O:21])[C:22](=[O:23])[N:24]2[CH2:25][CH2:26][N:27]([C:28](=[O:29])[c:30]3[cH:31][cH:32][cH:33][cH:34][cH:35]3)[CH2:36][CH2:37]2)[n:15][cH:14]1)=[O:13]>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6](-[c:7]... | COc1cnc(-c2cnc(C(=O)NC(C)(C)C)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | COc1cnc(-c2cnc(C(N)=O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | null | S(O)(O)(=O)=O | CO | Deprotection | Tert-butyl deprotection of amine | 362ce9f32fa9143425301d65e40d15ffd3094dc4b93d87814858041df496159d | 7dd4e31f8222caf32b51816846acd5aa4b71dcffacfd638f63f63fbb142a451d | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(-c3cnccn3)nccc12 | C-C(-C)(-C)-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:4](-[C:2](-[NH2;D1;+0:1])=[O;D1;H0:3]):[#7;a:5] | 5.5 | [{"value": 5.5, "product": "C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1N=CC(=NC1)C(=O)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | The compound of Example 15, 1-benzoyl-4-[(4-methoxy-7-(2-(1,1-dimethylethylaminocarbonyl)-pyrazin-5-yl)-6-azaindol-3-yl)-oxoacetyl]piperazine (20 mg) was dissolved in 1 drop of concentrated sulfuric acid. After 30 minutes, the mixture was diluted with 2 mL of methanol. The resulting solution was injected into a Shimadz... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amide | null | null | c1cnccn1.c1cc2cc[nH]c2cn1.C1C[NH]CC[NH]1.c1ccccc1 | Other | S(O)(O)(=O)=O.CO | null | 0.5 | COc1cnc(-c2cnc(C(=O)NC(C)(C)C)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12>S(O)(O)(=O)=O.CO>COc1cnc(-c2cnc(C(N)=O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e6e9d37612648bdb4e1a0138a1f96c2 | C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2nc(C#N)ccc12.[N-]=[N+]=[N-]>>C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2nc(-n3cnnn3)ccc12 | [NH4+].[Cl-].C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(C(=O)C1=CNC2=NC(=CC=C12)C#N)=O)C.[N-]=[N+]=[N-].[Na+].CN(C)C=O>>C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(C(=O)C1=CNC2=NC(=CC=C12)N1N=NN=C1)=O)C | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][N:15]1[C:16](=[O:17])[C:18](=[O:19])[c:20]1[cH:21][nH:22][c:23]2[n:24][c:25]([C:27]#[N:26])[cH:31][cH:32][c:33]12.[N-:28]=[N+:29]=[N-:30]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]... | C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2nc(C#N)ccc12.[N-]=[N+]=[N-] | C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2nc(-n3cnnn3)ccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 7ae20dcf12ec5149046f32595ef88500faa7ab11daa230990336f9be0a553259 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2nc(-n3cnnn3)ccc12 | [N-;H0;D1:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8](:[#7;a:9]:[c:10]):[c:11]:[c:12]:[c:13]:1>>[c:10]:[#7;a:9]:[c:8]1:[#7;a:7]:[c;H0;D3;+0:6](-[n;H0;D3;+0:4]2:[cH;D2;+0:5]:[n;H0;D2;+0:1]:[n;H0;D2;+0:2]:[n;H0;D2;+0:3]:2):[c:13]:[c:12]:[c:11]:1 | null | [] | null | null | null | null | An excess of NH4Cl (27 mg) was added into a solution of 1-(benzoyl)-3-(R)-methyl-4-[(6-cyano-7-azaindol-3-yl)-oxoacetyl]piperazine (20 mg) and NaN3 (16 mg) in DMF. The reaction was heated to reflux for 12 h. After cooling down, the mixture was concentrated under reduced pressure and the residue was purified using Shima... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1.c1nnn[nH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1cnc2[nH]ccc2c1.c1nnn[nH]1 | null | null | null | null | C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2nc(C#N)ccc12.[N-]=[N+]=[N-]>>C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(=O)c1c[nH]c2nc(-n3cnnn3)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19e6220357f9428e9de32ac0a883d830 | COc1ccc(-c2ccnc3c(C(=O)C(=O)[O-])c[nH]c23)cc1.O=C(c1ccccc1)N1CCNCC1>>COc1ccc(-c2ccnc3c(C(=O)C(=O)N4CCN(C(=O)c5ccccc5)CC4)c[nH]c23)cc1 | C(C)OP(=O)(OCC)ON1N=NC2=C(C1=O)C=CC=C2.C(C1=CC=CC=C1)(=O)N1CCNCC1.CCN(C(C)C)C(C)C.COC1=CC=C(C=C1)C=1C=CN=C2C(=CNC12)C(C(=O)[O-])=O.[K+]>>C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(C=CN=C12)C1=CC=C(C=C1)OC)=O | [O-][C:15]([C:13]([c:12]1[c:11]2[n:10][cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:35][cH:34]3)[c:33]2[nH:32][cH:31]1)=[O:14])=[O:16].[NH:17]1[CH2:18][CH2:19][N:20]([C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[CH2:29][CH2:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][... | COc1ccc(-c2ccnc3c(C(=O)C(=O)[O-])c[nH]c23)cc1.O=C(c1ccccc1)N1CCNCC1 | COc1ccc(-c2ccnc3c(C(=O)C(=O)N4CCN(C(=O)c5ccccc5)CC4)c[nH]c23)cc1 | null | null | CN(C)C=O | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(-c3ccccc3)ccnc12 | [#7;a:1]:[c:2]:[c:3](-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7]):[c:8]:[#7;a:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#7;a:1]:[c:2]:[c:3](-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1):[c:8]:[#7;a:9] | null | [] | null | null | 8 | HOUR | The procedure for the preparation of Examples 65-67 is the same as that described previously for the preparation of Precursor 5a and is as follows: Potassium 7-(4-methoxyphenyl)-4-azaindole-3-glyoxylate, Precursor 4c (147 mg, 0.44 mmol), an appropriate 1-benzoylpiperazine derivative (0.44 mmol), 3-(diethoxyphosphorylox... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1cnc2cc[nH]c2c1 | HO- | CN(C)C=O | null | 8 | COc1ccc(-c2ccnc3c(C(=O)C(=O)[O-])c[nH]c23)cc1.O=C(c1ccccc1)N1CCNCC1>CN(C)C=O>COc1ccc(-c2ccnc3c(C(=O)C(=O)N4CCN(C(=O)c5ccccc5)CC4)c[nH]c23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a22c84f01d9f4f098ff42a4c46a8d78f | CC1CN(C(=O)c2ccccc2)CCN1.COc1ccc(-c2ccnc3c(C(=O)C(=O)[O-])c[nH]c23)cc1>>COc1ccc(-c2ccnc3c(C(=O)C(=O)N4CCN(C(=O)c5ccccc5)C[C@H]4C)c[nH]c23)cc1 | C(C1=CC=CC=C1)(=O)N1CC(NCC1)C.COC1=CC=C(C=C1)C=1C=CN=C2C(=CNC12)C(C(=O)[O-])=O.[K+]>>C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(C(=O)C1=CNC2=C(C=CN=C12)C1=CC=C(C=C1)OC)=O)C | [NH:17]1[CH2:18][CH2:19][N:20]([C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[CH2:29][CH:30]1[CH3:31].[O-][C:15]([C:13]([c:12]1[c:11]2[n:10][cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36][cH:35]3)[c:34]2[nH:33][cH:32]1)=[O:14])=[O:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9]... | CC1CN(C(=O)c2ccccc2)CCN1.COc1ccc(-c2ccnc3c(C(=O)C(=O)[O-])c[nH]c23)cc1 | COc1ccc(-c2ccnc3c(C(=O)C(=O)N4CCN(C(=O)c5ccccc5)C[C@H]4C)c[nH]c23)cc1 | null | null | null | Acylation | OtherReaction | 93ea86207abfeff1b02bb7503ed10e691037e2837535fa3c9f36e53cad83f22a | 4cf1fe032f755d4c0d741720388859a41509db31ea6d3b11b3097630abef7487 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(-c3ccccc3)ccnc12 | [#7;a:1]:[c:2]:[c:3](-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7]):[c:8]:[#7;a:9].[C;D1;H3:10]-[CH;D3;+0:11]1-[C:12]-[#7:13](-[C:14]=[O;D1;H0:15])-[C:16]-[C:17]-[NH;D2;+0:18]-1>>[#7;a:1]:[c:2]:[c:3](-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:18]1-[C:17]-[C:16]-[#7:13](-[C:14]=[O;D1;H0:15])-... | null | [] | null | null | null | null | Example 67, 1-benzoyl-3-(R)-methyl-4-[(7-(4-methoxyphenyl)-4-azaindol-3-yl)oxoacetyl]piperazine was prepared from potassium 7-(4-methoxyphenyl)-4-azaindole-3-glyoxylate and the corresponding 1-benzoyl-3-methylpiperazine according to the above general procedure. MS m/z: (M+H)+ Calc'd for C28H27N4O4: 483.20; found 483.16... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Ketone.Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1cnc2cc[nH]c2c1 | HO- | null | null | null | CC1CN(C(=O)c2ccccc2)CCN1.COc1ccc(-c2ccnc3c(C(=O)C(=O)[O-])c[nH]c23)cc1>>COc1ccc(-c2ccnc3c(C(=O)C(=O)N4CCN(C(=O)c5ccccc5)C[C@H]4C)c[nH]c23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e28dee11518e4e9d97105c288d70e3e4 | COc1cnc(C2C=CC(=C=O)O2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12>>COc1cnc(-c2ccc(C(=O)O)o2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C1OC(C=C1)=C=O)=O.[O-]Cl=O.[Na+].CC#N>>C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C1=CC=C(O1)C(=O)O)=O | [CH3:1][O:2][c:3]1[cH:4][n:5][c:6]([CH:7]2[CH:8]=[CH:9][C:10](=[C:11]=[O:12])[O:14]2)[c:15]2[nH:16][cH:17][c:18]([C:19](=[O:20])[C:21](=[O:22])[N:23]3[CH2:24][CH2:25][N:26]([C:27](=[O:28])[c:29]4[cH:30][cH:31][cH:32][cH:33][cH:34]4)[CH2:35][CH2:36]3)[c:37]12>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6](-[c:7]2[cH:8][cH:9][c:10]... | COc1cnc(C2C=CC(=C=O)O2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | COc1cnc(-c2ccc(C(=O)O)o2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 953c21824281876c820a62d8ba7cfa59bcd3f37f8c63f565aa20028781e09002 | 12cc2fb631dd30ee6a50eb0cfe9972e5eccb28ef06b723d5cb2af2abd90fa766 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(-c3ccco3)nccc12 | [O;D1;H0:1]=[C;H0;D2;+0:2]=[C;H0;D3;+0:3]1-[CH;D2;+0:4]=[CH;D2;+0:5]-[CH;D3;+0:6](-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13])-[O;H0;D2;+0:14]-1>>[O;D1;H0:1]=[C;H0;D3;+0:2](-[O;D1;H1:15])-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10](:[c:11]):[#7;... | 25.5 | [{"value": 25.5, "product": "C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C1=CC=C(O1)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of the compound of Example 85 (19 mg), NaClO2 (9.2 mg) in a mixed solution of CH3CN (3 mL) and water (0.5 mL) was stirred at room temperature for 24 hours. After the reaction was quenched by 1N NaOH solution (1 ml), the mixture was extracted with diethyl ether (3×10 mL). The aqueous phase was acidified with 1... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Carboxylic acid | C1=CCOC1 | c1ccoc1 | c1ccoc1.c1cc2cc[nH]c2cn1.C1C[NH]CC[NH]1.c1ccccc1 | Other | O | null | 24 | COc1cnc(C2C=CC(=C=O)O2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12>O>COc1cnc(-c2ccc(C(=O)O)o2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7659f7731304f35912702b75b69a11e | CC(=O)OC(C)=O.COc1cnc(-c2cnc(N)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12>>COc1cnc(-c2cnc(NC(C)=O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1N=CC(=NC1)N)=O.C(C)(=O)OC(C)=O>>C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1N=CC(=NC1)NC(C)=O)=O | CC(=O)O[C:12]([CH3:13])=[O:14].[CH3:1][O:2][c:3]1[cH:4][n:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH2:11])[cH:15][n:16]2)[c:17]2[nH:18][cH:19][c:20]([C:21](=[O:22])[C:23](=[O:24])[N:25]3[CH2:26][CH2:27][N:28]([C:29](=[O:30])[c:31]4[cH:32][cH:33][cH:34][cH:35][cH:36]4)[CH2:37][CH2:38]3)[c:39]12>>[CH3:1][O:2][c:3]1[cH:4][n:5][... | CC(=O)OC(C)=O.COc1cnc(-c2cnc(N)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | COc1cnc(-c2cnc(NC(C)=O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | null | null | N1=CC=CC=C1 | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(-c3cnccn3)nccc12 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:1 | 69 | [{"value": 69.0, "product": "C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1N=CC(=NC1)NC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 1-(benzoyl)-4-[(4-methoxy-7-(2-amino-pyrazin-5-yl)-6-azaindol-3-yl)-oxoacetyl]piperazine (4 mg) and acetic anhydride (20 mg) were dissolved in pyridine (0.5 ml). The reaction was stirred for three hours at room temperature. After reaction was quenched with MeOH (1 ml), solvents were concentrated to give a residue which... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1cnccn1.c1cc2cc[nH]c2cn1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | N1=CC=CC=C1 | null | 3 | CC(=O)OC(C)=O.COc1cnc(-c2cnc(N)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12>N1=CC=CC=C1>COc1cnc(-c2cnc(NC(C)=O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6432ec65c7d41019b51210b8bb20865 | COc1cnc(-c2cnc(N)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12.O=S(=O)(O)O>>COc1cnc(-c2cnc(O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1N=CC(=NC1)N)=O.N(=O)[O-].[Na+].OS(=O)(=O)O>>C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1N=CC(=NC1)O)=O | N[c:10]1[n:9][cH:8][c:7](-[c:6]2[n:5][cH:4][c:3]([O:2][CH3:1])[c:36]3[c:14]2[nH:15][cH:16][c:17]3[C:18](=[O:19])[C:20](=[O:21])[N:22]2[CH2:23][CH2:24][N:25]([C:26](=[O:27])[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[CH2:34][CH2:35]2)[n:13][cH:12]1.O=S(=O)(O)[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6](-[c:7]2[cH:8][n:9... | COc1cnc(-c2cnc(N)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12.O=S(=O)(O)O | COc1cnc(-c2cnc(O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | null | null | C(=O)([O-])[O-].[Na+].[Na+] | Heteroatom Alkylation and Arylation | OtherReaction | 2be561f346be58728fb097078553d70a1915acea426fd1f5d78febc41949eb49 | 0faab53fb44f5d790c940e8273c888214a6763f53a41b0c03d0241319b9333e9 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(-c3cnccn3)nccc12 | N-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.O-S(=O)(=O)-[OH;D1;+0:7]>>[OH;D1;+0:7]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 27.9 | [{"value": 27.9, "product": "C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1N=CC(=NC1)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 1-(benzoyl)-4-[(4-methoxy-7-(2-amino-pyrazin-5-yl)-6-azaindol-3-yl)-oxoacetyl]piperazine (15 mg) and NaNO2 (10 mg) was added into a H2SO4 solution (0.1 ml of concentrated H2SO4 diluted with 0.3 ml of water). The reaction was stirred at room temperature for one hour. Then, the reaction mixture was neutralized with a sat... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic alcohol | c1cnccn1 | c1cnccn1 | c1cnccn1.c1cc2cc[nH]c2cn1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | C(=O)([O-])[O-].[Na+].[Na+] | null | 1 | COc1cnc(-c2cnc(N)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12.O=S(=O)(O)O>C(=O)([O-])[O-].[Na+].[Na+]>COc1cnc(-c2cnc(O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e2fd5c21d5a441d4ae635666059f02aa | CI.COc1cnc(-c2cnc(O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12>>COc1cnc(-c2cn(C)c(=O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1N=CC(=NC1)O)=O.CI.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1N=CC(N(C1)C)=O)=O | I[CH3:10].[CH3:1][O:2][c:3]1[cH:4][n:5][c:6](-[c:7]2[cH:8][n:9][c:11]([OH:12])[cH:13][n:14]2)[c:15]2[nH:16][cH:17][c:18]([C:19](=[O:20])[C:21](=[O:22])[N:23]3[CH2:24][CH2:25][N:26]([C:27](=[O:28])[c:29]4[cH:30][cH:31][cH:32][cH:33][cH:34]4)[CH2:35][CH2:36]3)[c:37]12>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6](-[c:7]2[cH:8][n:9... | CI.COc1cnc(-c2cnc(O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | COc1cnc(-c2cn(C)c(=O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 | null | null | CC(=O)C | Acylation | OtherReaction | 6f5585bd0f38e612015251a389b1ca2d1522e73ef1984c05573fa7f4f9536c13 | 112bab89a832807e83a4911f32b3895489765458263eca889524c8ed19f7b9da | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(-c3c[nH]c(=O)cn3)nccc12 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3]:[c:4](-[c:5]1:[#7;a:6]:[c:7]:[c;H0;D3;+0:8](-[OH;D1;+0:9]):[n;H0;D2;+0:10]:[c:11]:1):[#7;a:12]>>[#7;a:2]:[c:3]:[c:4](-[c:5]1:[#7;a:6]:[c:7]:[c;H0;D3;+0:8](=[O;H0;D1;+0:9]):[n;H0;D3;+0:10](-[CH3;D1;+0:1]):[c:11]:1):[#7;a:12] | 48.6 | [{"value": 48.6, "product": "C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC2=C(N=CC(=C12)OC)C=1N=CC(N(C1)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 1-(benzoyl)-4-[(4-methoxy-7-(2-hydroxyl-pyrazin-5-yl)-6-azaindol-3-yl)-oxoacetyl]piperazine (6 mg), MeI (5 mg) and K2CO3 (4 mg) were dissolved in acetone (5 ml). The reaction was stirred for four hours at room temperature. After solid was filtered away, the mother liquid was concentrated to give a residue which was pur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | null | c1cnccn1 | c1cnccn1 | c1cnccn1.c1cc2cc[nH]c2cn1.C1C[NH]CC[NH]1.c1ccccc1 | HI | CC(=O)C | null | 4 | CI.COc1cnc(-c2cnc(O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12>CC(=O)C>COc1cnc(-c2cn(C)c(=O)cn2)c2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fbcb8c8d54b144f9bc84e76f14379c36 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Cl)ccnc12.c1c[nH]nn1>>O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(-n3nccn3)ccnc12 | C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC=2C1=NC=CC2Cl)=O.N1N=NC=C1.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(C(=O)C1=CNC=2C1=NC=CC2N2N=CC=N2)=O | Cl[c:23]1[c:22]2[nH:21][cH:20][c:19]([C:2](=[O:1])[C:3](=[O:4])[N:5]3[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]4[cH:12][cH:13][cH:14][cH:15][cH:16]4)[CH2:17][CH2:18]3)[c:32]2[n:31][cH:30][cH:29]1.[nH:24]1[n:25][n:28][cH:27][cH:26]1>>[O:1]=[C:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][cH... | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Cl)ccnc12.c1c[nH]nn1 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(-n3nccn3)ccnc12 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 7cc06b870bf955d83920bd5ad6889455b32223e96b9fa682763620ddbbd83b7f | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(-n3nccn3)ccnc12 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6](-[C:7]=[O;D1;H0:8]):[c:9]:[#7;a:10]:[c:11]:2:1.[c:12]1:[cH;D2;+0:13]:[nH;D2;+0:14]:[n;H0;D2;+0:15]:[n;H0;D2;+0:16]:1>>[O;D1;H0:8]=[C:7]-[c:6]1:[c:9]:[#7;a:10]:[c:11]2:[c:5]:1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[n;H0;D3;+0:14]1:[n;H0;D2;+0:15]:[cH;D2;+0:13]:[c:12]:... | null | [] | null | null | null | null | Example 205 and 206. In a sealed tube -(4-benzoyl-piperazin-1-yl)-2-(7-chloro-1H-pyrrolo[3,2-b]pyridin-3-yl)-ethane-1,2-dione (30 mg, 0.076 mmol), 1H-1,2,3-triazole (160 mg, 2.3 mmol), Cu (0) (10 mg, 0.16 mmol) and K2CO3 (11 mg, 0.080 mmol) were heated at 160° C. for 16 h. The reaction mixture was diluted with MeOH, fi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cnc2cc[nH]c2c1.c1c[nH]nn1 | c1c[nH]nn1.c1cnc2cc[nH]c2c1 | C1C[NH]CC[NH]1.c1ccccc1.c1c[nH]nn1.c1cnc2cc[nH]c2c1 | HCl | CO | null | null | O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(Cl)ccnc12.c1c[nH]nn1>CO>O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2c(-n3nccn3)ccnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-862ea87eca914bbd98c1a3b73a3d32d3 | C=O.O=c1cc[nH]c(=O)[nH]1>>O=c1[nH]cc(CO)c(=O)[nH]1 | N1C(=O)NC(=O)C=C1.N1C(=O)NC(=O)C=C1.C=O.[OH-].[K+]>>OCC=1C(NC(NC1)=O)=O | [CH2:6]=[O:7].[O:1]=[c:2]1[nH:3][cH:4][cH:5][c:8](=[O:9])[nH:10]1>>[O:1]=[c:2]1[nH:3][cH:4][c:5]([CH2:6][OH:7])[c:8](=[O:9])[nH:10]1 | C=O.O=c1cc[nH]c(=O)[nH]1 | O=c1[nH]cc(CO)c(=O)[nH]1 | null | null | O | C-C Coupling | OtherReaction | 67448c64d4a30a61f5e502af4acf85fb4cc3d0f5db899aa52bfc35f9dce8fff1 | 4396295d899f5d4f5de2e844a80fc7d194b4da158f49df3d2717206b401b59bd | O=c1cc[nH]c(=O)[nH]1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[O;D1;H0:3]=[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[cH;D2;+0:9]:1>>[O;D1;H0:3]=[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c;H0;D3;+0:9]:1-[CH2;D2;+0:1]-[OH;D1;+0:2] | 54.4 | [{"value": 54.4, "product": "OCC=1C(NC(NC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | To a 40 mL aqueous solution containing 0.60 gram of KOH were added 1.2 g of uracil and 5 mL of a 36.5% aqueous solution of formaldehyde. The resulting mixture was stirred in an oil bath set at 50° C. and the reaction was allowed to proceed until the complete disappearance of the starting uracil as observed by thin laye... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary alcohol | c1ccncn1 | c1cncnc1 | c1cncnc1 | null | O | null | 72 | C=O.O=c1cc[nH]c(=O)[nH]1>O>O=c1[nH]cc(CO)c(=O)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2279370aa0c2485cbfa231929bf5bf2b | O=c1[nH]c(=O)n(Cc2ccccc2)cc1Br>>O=c1ccn(Cc2ccccc2)c(=O)[nH]1 | BrBr.C(C1=CC=CC=C1)N1C(=O)NC(=O)C(=C1)Br>>C(C1=CC=CC=C1)N1C(=O)NC(=O)C=C1 | Br[c:3]1[c:2](=[O:1])[nH:15][c:13](=[O:14])[n:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:4]1>>[O:1]=[c:2]1[cH:3][cH:4][n:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13](=[O:14])[nH:15]1 | O=c1[nH]c(=O)n(Cc2ccccc2)cc1Br | O=c1ccn(Cc2ccccc2)c(=O)[nH]1 | null | null | CS(=O)C.CN(C=O)C | Functional Group Interconversion | Aromatic dehalogenation | 895159d874869aa7a3c29ba9f3a6fce27d4e3f1b326a7f3ea2a46c97ca88bc67 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=c1ccn(Cc2ccccc2)c(=O)[nH]1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[C:4]):[c:5]:[#7;a:6]:[c:7]:1=[O;D1;H0:8]>>[C:4]-[#7;a:3]1:[c:5]:[#7;a:6]:[c:7](=[O;D1;H0:8]):[cH;D2;+0:1]:[c:2]:1 | null | [] | null | null | null | null | This experiment was performed to verify the role of DMSO solvent in the generation of the bromine electrophile. Thus, this synthesis was done following the same procedure as for the synthesis of 1-benzyl-5-bromouracil, with the sole exception that DMSO was replaced by dimethylformamide (DMF), as solvent. Extraction was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cncnc1 | c1ccncn1 | c1ccncn1.c1ccccc1 | Br- | CS(=O)C.CN(C=O)C | null | null | O=c1[nH]c(=O)n(Cc2ccccc2)cc1Br>CS(=O)C.CN(C=O)C>O=c1ccn(Cc2ccccc2)c(=O)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e381f6d16db417595dcaa7f6ee26e2a | BrCc1ccccc1.C#CCCCC.O=c1[nH]cc(I)c(=O)[nH]1>>CCCCC#Cc1c[nH]c(=O)[nH]c1=O.CCCCc1cc2c(cnc(=O)n2Cc2ccccc2)o1 | C(CCC)C1=CC2=C(C=NC(N2)=O)O1.IC=1C(NC(NC1)=O)=O.C#CCCCC.C(C1=CC=CC=C1)Br>>C(#CCCCC)C=1C(NC(NC1)=O)=O.C(CCC)C1=CC2=C(C=NC(N2)=O)O1.C(C1=CC=CC=C1)N1C(N=CC2=C1C=C(O2)CCCC)=O | Br[CH2:42][c:43]1[cH:29][cH:47][cH:46][cH:45][cH:44]1.[CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[CH:6].I[c:7]1[cH:8][nH:9][c:10](=[O:11])[nH:12][c:13]1=[O:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][nH:9][c:10](=[O:11])[nH:12][c:13]1=[O:14].[CH3:29][CH2:30][CH2:31][CH2:32][c:33]1[cH:34][c:35]2[c:36]([cH:37][n:38][... | BrCc1ccccc1.C#CCCCC.O=c1[nH]cc(I)c(=O)[nH]1 | CCCCC#Cc1c[nH]c(=O)[nH]c1=O.CCCCc1cc2c(cnc(=O)n2Cc2ccccc2)o1 | null | null | [OH-].[K+].CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | e97fb092360d25824396040225e85cb1cb7423c26b8a53750aebc2f071c3ef0a | 9418fed7c76a32c5582c05acffdfdf149cfd56a6866d03b350e5b9843d82c5fb | O=c1cc[nH]c(=O)[nH]1.O=c1ncc2occc2n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:1.I-[c;H0;D3;+0:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1=[O;D1;H0:14].[C:15]-[C:16]#[CH;D1;+0:17]>>[C:15]-[C:16]#[C;H0;D2;+0:17]-[c;H0;D3;+0:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1=[O;D1;H0:14].[C:18]-[C:19]-[CH3;D1;+0:7].[c:20]:[#7... | null | [] | 65 | CELSIUS | null | null | As above, 5-hexynyluracil and 6-n-butylfuranopyrimidin-2-one was prepared from 3.0 g of 5-iodouracil and 3.0 mL of 1-hexyne at 50° C. for 24 hours. Triethylamine solvent was completely distilled off at reduced pressure and a pale yellow slurry was obtained. This slurry was dissolved in 50.0 mL of DMF containing 0.70 g ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Alkyne | Alkyne | c1ccccc1.c1cncnc1 | c1cncnc1.c1ncc2occc2n1.c1ccccc1 | c1cncnc1.c1ncc2occc2n1.c1ccccc1 | Br-.I- | [OH-].[K+].CN(C)C=O | 65 | null | BrCc1ccccc1.C#CCCCC.O=c1[nH]cc(I)c(=O)[nH]1>[OH-].[K+].CN(C)C=O>CCCCC#Cc1c[nH]c(=O)[nH]c1=O.CCCCc1cc2c(cnc(=O)n2Cc2ccccc2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5bf956ae3e7d4f2da03b80ec3324ad2f | Cc1cc(Nc2ncnc3ccc(C(O)C(O)CNC(=O)OC(C)(C)C)cc23)ccc1Oc1ccccc1>>Cc1cc(Nc2ncnc3ccc(C=O)cc23)ccc1Oc1ccccc1 | C(C)(C)(C)OC(NCC(C(C=1C=C2C(=NC=NC2=CC1)NC1=CC(=C(C=C1)OC1=CC=CC=C1)C)O)O)=O>>CC=1C=C(C=CC1OC1=CC=CC=C1)NC1=NC=NC2=CC=C(C=C12)C=O | CC(C)(C)OC(=O)NCC(O)[CH:14]([c: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][cH:26][cH:27]4)[cH:19][cH:18]3)[c:17]2[cH:16]1)[OH:15]>>[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][c:13]([CH:14]=[O:15])[cH:16][c:17]23)... | Cc1cc(Nc2ncnc3ccc(C(O)C(O)CNC(=O)OC(C)(C)C)cc23)ccc1Oc1ccccc1 | Cc1cc(Nc2ncnc3ccc(C=O)cc23)ccc1Oc1ccccc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 922fe848b6ff44c0859c63aae61f648fcd5286c05a204fa52add7482d3ad80ac | b0edb1c1385e81f771fbc7b12ce6338de1981c6ceb9604fd20e26a035820923e | c1ccc(Oc2ccc(Nc3ncnc4ccccc34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-N-C-C(-O)-[CH;D3;+0:1](-[OH;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | 4-(3-Methyl-4-phenoxy-phenylamino)-quinazoline-6-carbaldehyde is prepared by adding NaIO4 (1.5 mL, 0.65 M in H2O) to a slurry of silica gel (1 g) in DCM (6 mL) followed by the addition of {2,3-dihydroxy-3-[4-(3-methyl-4-phenoxy-phenylamino)-quinazolin-6-yl]-propyl}-carbamic acid tert-butyl ester (from Step A, ˜0.64 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Secondary alcohol.Secondary alcohol.Boc | Aldehyde | null | null | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1 | HO- | C(Cl)Cl | null | 1 | Cc1cc(Nc2ncnc3ccc(C(O)C(O)CNC(=O)OC(C)(C)C)cc23)ccc1Oc1ccccc1>C(Cl)Cl>Cc1cc(Nc2ncnc3ccc(C=O)cc23)ccc1Oc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-81ce7f23e4094c1abfe863bea92b1be0 | C#CCNC(=O)OC(C)(C)C.Fc1cccc(COc2ccc(Nc3ncnc4ccc(I)cc34)cc2Cl)c1>>CC(C)(C)OC(=O)NCC#Cc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1 | C(C)(C)(C)OC(NCC#C)=O.C(C)(C)NC(C)C.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC1=NC=NC2=CC=C(C=C12)I>>C(C)(C)(C)OC(NCC#CC=1C=C2C(=NC=NC2=CC1)NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]#[CH:11].I[c: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][CH2:26][c:27]4[cH:28][cH:29][cH:30][c:31]([F:32])[cH:33]4)[c:34]([Cl:35])[cH:36]3)[c:37]2[cH:38]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])... | C#CCNC(=O)OC(C)(C)C.Fc1cccc(COc2ccc(Nc3ncnc4ccc(I)cc34)cc2Cl)c1 | CC(C)(C)OC(=O)NCC#Cc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C1CCOC1 | C-C Coupling | Sonogashira alkyne_aryl halide | 872429a8a448d5fe6a6d8e65a972b06e01987bec74a5bcedc0bc9d34c8be3a80 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc(COc2ccc(Nc3ncnc4ccccc34)cc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:[#7;a:8]):[c:9]:1.[C:10]-[C:11]#[CH;D1;+0:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:12]#[C:11]-[C:10]):[c:9]:[c:6]:1:[c:7]:[#7;a:8] | null | [] | null | null | 3 | HOUR | (3-{4-[3 -Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-yl}-prop-2-ynyl)-carbamic acid tert-butyl ester is prepared by adding prop-2-ynyl-carbamic acid tert-butyl ester (0.978 g, 6.31 mmol), diisopropylamine (1.77 ml, 12.63 mmol), Pd(PPh3)2Cl2 (210 mg, 0.30 mmol) and CuI (57 mg, 0.30 mmol) to a stirred soluti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C1CCOC1 | null | 3 | C#CCNC(=O)OC(C)(C)C.Fc1cccc(COc2ccc(Nc3ncnc4ccc(I)cc34)cc2Cl)c1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C1CCOC1>CC(C)(C)OC(=O)NCC#Cc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a498fed478945c6b1375adfee8581c0 | CC(C)(C)OC(=O)NCC#Cc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1>>CC(C)(C)OC(=O)NCC=Cc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1 | COCCO[AlH2-]OCCOC.[Na+].C(C)(C)(C)OC(NCC#CC=1C=C2C(=NC=NC2=CC1)NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl)=O>>C(C)(C)(C)OC(NCC=CC=1C=C2C(=NC=NC2=CC1)NC1=CC(=C(C=C1)OCC1=CC(=CC=C1)F)Cl)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]#[C:11][c: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][CH2:26][c:27]4[cH:28][cH:29][cH:30][c:31]([F:32])[cH:33]4)[c:34]([Cl:35])[cH:36]3)[c:37]2[cH:38]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH... | CC(C)(C)OC(=O)NCC#Cc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1 | CC(C)(C)OC(=O)NCC=Cc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1 | null | null | C1(=CC=CC=C1)C.C1CCOC1 | Reduction | Hydrogenation (triple to double) | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(COc2ccc(Nc3ncnc4ccccc34)cc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9]-[C;H0;D2;+0:10]#[C;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14] | 67 | [{"value": 67.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | (3-{4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-yl}-allyl)-carbamic acid tert-butyl ester is prepared by adding (3-{4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-yl}-prop-2-ynyl)-carbamic acid tert-butyl ester (3.00 g, 5.63 mmol) to a mixture of Red-Al (5 ml of a 65% wt solution in tolue... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C.C1CCOC1 | 0 | 3 | CC(C)(C)OC(=O)NCC#Cc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1>C1(=CC=CC=C1)C.C1CCOC1>CC(C)(C)OC(=O)NCC=Cc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d18fde1d49f04a0dbb4d002daebf2a3f | CNN.CSC1=NCCN1C>>CN(N)C1=NCCN1C | CN1C(=NCC1)SC.CNN>>CN(N)C=1N(CCN1)C | [CH3:1][NH:2][NH2:3].CS[C:4]1=[N:5][CH2:6][CH2:7][N:8]1[CH3:9]>>[CH3:1][N:2]([NH2:3])[C:4]1=[N:5][CH2:6][CH2:7][N:8]1[CH3:9] | CNN.CSC1=NCCN1C | CN(N)C1=NCCN1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a8d32681f2835d586883c31ce8e73ea12f0adf851c77848d95536099dcbf3b3e | aa2f419776abe47456a5312ece2d45d826775197fbe6bdfbc423243ab902a828 | C1=NCCN1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3]-[C:4]-[#7:5]-1-[C;D1;H3:6].[C;D1;H3:7]-[NH;D2;+0:8]-[N;D1;H2:9]>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[N;D1;H2:9])-[C;H0;D3;+0:1]1=[#7:2]-[C:3]-[C:4]-[#7:5]-1-[C;D1;H3:6] | null | [] | null | null | null | null | N-Methyl-N-(1-methyl-4,5-dihydro-1 H-imidazol-2-yl)-hydrazine is prepared according to Step B of Example 25 using 1-methyl-2-methylsulfanyl-4,5-dihydro-1 H-imidazole and methyl hydrazine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Monosulfide | Hydrazine | C1=NCC[NH]1 | C1=NCC[NH]1 | C1=NCC[NH]1 | Other | null | null | null | CNN.CSC1=NCCN1C>>CN(N)C1=NCCN1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87d9d2d9ebbd4c55aa6b5c61a5d99f8c | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CN(C)CC(N)C(=O)O.CN(C)CC(N)C(=O)O>>CN(C)CC(NC(=O)OC(C)(C)C)C(=O)O.CNC(CO)CN(C)C | Cl.Cl.NC(CN(C)C)C(=O)O.C(=O)(OC(C)(C)C)OC(=O)OC(C)(C)C.Cl.Cl.NC(CN(C)C)C(=O)O.C(=O)([O-])[O-].[Na+].[Na+]>>CN(CC(CO)NC)C.C(C)(C)(C)OC(=O)NC(C(=O)O)CN(C)C | CC(C)(C)OC(=O)O[C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13].O=[C:20]([CH:19]([NH2:18])[CH2:22][N:23]([CH3:24])[CH3:25])[OH:21].[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]([NH2:6])[C:14](=[O:15])[OH:16]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C:14](=[O:15])[OH:16].[... | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CN(C)CC(N)C(=O)O.CN(C)CC(N)C(=O)O | CN(C)CC(NC(=O)OC(C)(C)C)C(=O)O.CNC(CO)CN(C)C | null | null | CC#N | Protection | OtherReaction | 5fa12acd554ead49eacff693a652d52f2d4e60a204f44593f6eeb4b63f3bdcde | ed24a0a54cdcaf3b4dacd9c809b3a2761a447f6a65ed01844cb7c8a432c480d7 | null | C-C(-C)(-C)-O-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].O=[C;H0;D3;+0:8](-[O;D1;H1:9])-[C:10](-[C:11])-[NH2;D1;+0:12].[C:13]-[C:14](-[NH2;D1;+0:15])-[C:16](=[O;D1;H0:17])-[O;D1;H1:18]>>[C:11]-[C:10](-[CH2;D2;+0:8]-[O;D1;H1:9])-[NH;D2;+0:12]-[C;D1;H3:19].[C:13]-[C:14](-[NH... | 31 | [{"value": 31.0, "product": "C(C)(C)(C)OC(=O)NC(C(=O)O)CN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 3-Dimethylamino-2-methylamino-propan-1-ol is prepared from 4-aza-DL-leucine 2 HCl. Di-tert-butyl dicarbonate (0.65 g, 2.97 mmol) is added to a biphasic mixture of 4-aza-DL-leucine 2 HCl (0.51 g, 2.47 mmol) in 10 ml 1:1 10% Na2CO3:MeCN. After stirring 16 hours, the MeCN is removed under reduced pressure and the aqueous ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Ester.Carbonic Ester.Carboxylic acid.Primary amine.Primary amine.Boc.Boc | Carbamic ester.Ether.Primary alcohol.Secondary amine.Boc | null | null | null | HO- | CC#N | null | 16 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CN(C)CC(N)C(=O)O.CN(C)CC(N)C(=O)O>CC#N>CN(C)CC(NC(=O)OC(C)(C)C)C(=O)O.CNC(CO)CN(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-066e94bb102e40e2a79c0921e0f00626 | CN1C(=Nc2ccc3ncnc(Nc4ccc(COc5cccc(F)c5)c(Cl)c4)c3c2)OC[C@@H]1COC(C)(C)C>>CN1C(=Nc2ccc3ncnc(Nc4ccc(COc5cccc(F)c5)c(Cl)c4)c3c2)OC[C@@H]1CO | C(C)(C)(C)OC[C@@H]1N(C(OC1)=NC=1C=C2C(=NC=NC2=CC1)NC1=CC(=C(C=C1)COC1=CC(=CC=C1)F)Cl)C.C(=O)(C(F)(F)F)O.C(C)(C)(C)OC[C@@H]1N(C(OC1)=NC=1C=C2C(=NC=NC2=CC1)NC1=CC(=C(C=C1)COC1=CC(=CC=C1)F)Cl)C>>ClC=1C=C(C=CC1COC1=CC(=CC=C1)F)NC1=NC=NC2=CC=C(C=C12)N=C1OC[C@@H](N1C)CO | CC(C)(C)[O:36][CH2:35][C@@H:34]1[N:2]([CH3:1])[C:3](=[N:4][c:5]2[cH:6][cH:7][c:8]3[n:9][cH:10][n:11][c:12]([NH:13][c:14]4[cH:15][cH:16][c:17]([CH2:18][O:19][c:20]5[cH:21][cH:22][cH:23][c:24]([F:25])[cH:26]5)[c:27]([Cl:28])[cH:29]4)[c:30]3[cH:31]2)[O:32][CH2:33]1>>[CH3:1][N:2]1[C:3](=[N:4][c:5]2[cH:6][cH:7][c:8]3[n:9][c... | CN1C(=Nc2ccc3ncnc(Nc4ccc(COc5cccc(F)c5)c(Cl)c4)c3c2)OC[C@@H]1COC(C)(C)C | CN1C(=Nc2ccc3ncnc(Nc4ccc(COc5cccc(F)c5)c(Cl)c4)c3c2)OC[C@@H]1CO | null | null | ClCCCl.C(Cl)Cl | Deprotection | Ether cleavage to primary alcohol | 9614211a2a35d6177bcded67d8911ba46072c6f11693f23436d14d3c121d33af | 29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609 | c1ccc(OCc2ccc(Nc3ncnc4ccc(N=C5NCCO5)cc34)cc2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[#7:4]>>[#7:4]-[C:3]-[C:2]-[OH;D1;+0:1] | 64 | [{"value": 64.0, "product": "ClC=1C=C(C=CC1COC1=CC(=CC=C1)F)NC1=NC=NC2=CC=C(C=C12)N=C1OC[C@@H](N1C)CO", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | (S)-(2-{4-[3-Chloro-4-(3-fluoro-phenoxymethyl)-phenylamino]-quinazolin-6-ylimino-}-3-methyl-oxazolidin-4-yl)-methanol is prepared from (S)-N6-(4-tert-butoxymethyl-3-methyl-oxazolidin-2-ylidene)-N4-[3-chloro-4-(3-fluoro-phenoxymethyl)-phenyl-]quinazoline-4,6-diamine. TFA (1 ml) is added to (S)-N6-(4-tert-butoxymethyl-3-... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | null | null | C1COC[NH]1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | Other | ClCCCl.C(Cl)Cl | 0 | 3 | CN1C(=Nc2ccc3ncnc(Nc4ccc(COc5cccc(F)c5)c(Cl)c4)c3c2)OC[C@@H]1COC(C)(C)C>ClCCCl.C(Cl)Cl>CN1C(=Nc2ccc3ncnc(Nc4ccc(COc5cccc(F)c5)c(Cl)c4)c3c2)OC[C@@H]1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d555a03d75e14d81987575d28d4faae2 | CC(C)(C)OC(=O)N1CC=CC1.CCCO.O=C([O-])NCc1ccccc1>>CC(C)(C)OC(=O)N1CC(O)C(NC(=O)OCc2ccccc2)C1 | C(C)(C)(C)OC(=O)N1CC=CC1.C(CC)O.S(=O)([O-])[O-].[Na+].[Na+].C(C1=CC=CC=C1)NC([O-])=O.ClN1C(=O)N(C(=O)C1(C)C)Cl.CCCO>>C(C)(C)(C)OC(=O)N1CC(C(C1)O)NC(=O)OCC1=CC=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]=[CH:12][CH2:24]1.CCC[OH:11].[NH:13]([C:14](=[O:15])[O-:16])[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([OH:11])[CH:12]([NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]2[cH:19][cH:... | CC(C)(C)OC(=O)N1CC=CC1.CCCO.O=C([O-])NCc1ccccc1 | CC(C)(C)OC(=O)N1CC(O)C(NC(=O)OCc2ccccc2)C1 | null | null | O.CCOC(=O)C.[OH-].[Na+] | Heteroatom Alkylation and Arylation | OtherReaction | a5989800986d9d85b11df2f60d1fc2645d53697a31c586035d6dd4bedef86b2e | d85457ee3872965b128c3c5c702e618322cc4f5f39e9a39355438cad3a97a51e | O=C(NC1CCNC1)OCc1ccccc1 | C-C-C-[OH;D1;+0:1].[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[C:7](=[O;D1;H0:8])-[#7:9]1-[C:10]-[CH;D2;+0:11]=[CH;D2;+0:12]-[C:13]-1.[O-;H0;D1:14]-[C:15](=[O;D1;H0:16])-[NH;D2;+0:17]-[CH2;D2;+0:18]-[c:19](:[c:20]):[c:21]>>[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[C:7](=[O;D1;H0:8])-[#7:9]1-[C:10]... | null | [] | 0 | CELSIUS | 1 | HOUR | N-Propanol (20 ml), benzylcarbamate (4 g, 27 mmol), and 1 ,3-dichloro-5,5-dimethylhydantoin (2.6 g, 13 mmol) are added to a solution of NaOH (1 g, 27 mmol) in water (40 ml). The reaction mixture is cooled to 0° C. and a solution of 2,5-dihydro-pyrrole-1 -carboxylic acid tert-butyl ester (1.51 g, 8.92 mmol) in n-propano... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic acid.Primary alcohol | Carbamic ester.Ether.Secondary alcohol | C1=CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | Other | O.CCOC(=O)C.[OH-].[Na+] | 0 | 1 | CC(C)(C)OC(=O)N1CC=CC1.CCCO.O=C([O-])NCc1ccccc1>O.CCOC(=O)C.[OH-].[Na+]>CC(C)(C)OC(=O)N1CC(O)C(NC(=O)OCc2ccccc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-010bd08ef7d143ec9d0b4a56a6da7160 | CC(C)(C)OC(=O)N1CC(O)C(NC(=O)OCc2ccccc2)C1>>CNC1CN(C)CC1O | [H-].[H-].[H-].[H-].[Li+].[Al+3].C(C)(C)(C)OC(=O)N1CC(C(C1)O)NC(=O)OCC1=CC=CC=C1>>CN1CC(C(C1)NC)O | CC(C)(C)O[C:6](=O)[N:5]1[CH2:4][CH:3]([NH:2][C:1](=O)OCc2ccccc2)[CH:8]([OH:9])[CH2:7]1>>[CH3:1][NH:2][CH:3]1[CH2:4][N:5]([CH3:6])[CH2:7][CH:8]1[OH:9] | CC(C)(C)OC(=O)N1CC(O)C(NC(=O)OCc2ccccc2)C1 | CNC1CN(C)CC1O | null | null | C1CCOC1 | Reduction | OtherReaction | 1e7b64761af7c80bc8809716a33b6671f058a2cb464dac5e237c543543240d89 | 105652e82dc6e2e1d3de36472a598a10c5c56bf1db0554400c8747307416bdc3 | C1CCNC1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=O)-[#7:2](-[C:3])-[C:4]-[C:5]-[#7:6]-[C;H0;D3;+0:7](=O)-O-C-c1:c:c:c:c:c:1>>[C:3]-[#7:2](-[CH3;D1;+0:1])-[C:4]-[C:5]-[#7:6]-[CH3;D1;+0:7] | 18 | [{"value": 18.0, "product": "CN1CC(C(C1)NC)O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | LAH (1.40 g, 35.0 mmol) is slowly added to a stirred solution of 3-benzyloxycarbonylamino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester in THF (15 ml) at room temperature. The reaction mixture is heated to reflux under N2 for 2 hours and then cooled to 0° C. The reaction mixture is quenched by the slow addit... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc | null | c1ccccc1 | null | C1CC[NH]C1 | HO- | C1CCOC1 | 0 | null | CC(C)(C)OC(=O)N1CC(O)C(NC(=O)OCc2ccccc2)C1>C1CCOC1>CNC1CN(C)CC1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-985532295722483ba0fcf54e9aaada80 | O=[N+]([O-])c1ccc(F)c(Cl)c1.OCc1nccs1>>O=[N+]([O-])c1ccc(OCc2nccs2)c(Cl)c1 | O.S1C(=NC=C1)CO.[H-].[Na+].ClC1=C(C=CC(=C1)[N+](=O)[O-])F>>ClC1=C(OCC=2SC=CN2)C=CC(=C1)[N+](=O)[O-] | F[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:17][c:15]1[Cl:16].[OH:8][CH2:9][c:10]1[n:11][cH:12][cH:13][s:14]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[n:11][cH:12][cH:13][s:14]2)[c:15]([Cl:16])[cH:17]1 | O=[N+]([O-])c1ccc(F)c(Cl)c1.OCc1nccs1 | O=[N+]([O-])c1ccc(OCc2nccs2)c(Cl)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(OCc2nccs2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[#16;a:7]:[c:8](-[C:9]-[OH;D1;+0:10]):[#7;a:11]>>[#16;a:7]:[c:8](-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6]):[#7;a:11] | 99.2 | [{"value": 99.0, "product": "ClC1=C(OCC=2SC=CN2)C=CC(=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.2, "product": "ClC1=C(OCC=2SC=CN2)C=CC(=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 2-(2-Chloro-4-nitro-phenoxymethyl)-thiazole is prepared by adding thiazol-2-yl-methanol (2.74 g, 23.76 mmol) to a slurry of sodium hydride (1.21 g of a 60% dispersion in oil, 30.2 mmol) in DMF (10 ml) at 0° C. After several minutes, 2-chloro-1-fluoro-4-nitro-benzene (3.79 g, 21.60 mmol) is added and the reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cscn1 | HF | CN(C)C=O | null | 3 | O=[N+]([O-])c1ccc(F)c(Cl)c1.OCc1nccs1>CN(C)C=O>O=[N+]([O-])c1ccc(OCc2nccs2)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fdaaf12318204a90ac517e6ccd5a3a9a | O=[N+]([O-])c1ccc(OCc2nccs2)c(Cl)c1.[NH4+]>>Nc1ccc(OCc2nccs2)c(Cl)c1.Nc1ccccc1 | ClC1=C(OCC=2SC=CN2)C=CC(=C1)[N+](=O)[O-].[NH4+].[Cl-]>>ClC=1C=C(C=CC1OCC=1SC=CN1)N.C1(=CC=CC=C1)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][c:8]2[n:9][cH:10][cH:11][s:12]2)[c:13]([Cl:14])[cH:15]1.[NH4+:16]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][c:8]2[n:9][cH:10][cH:11][s:12]2)[c:13]([Cl:14])[cH:15]1.[NH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | O=[N+]([O-])c1ccc(OCc2nccs2)c(Cl)c1.[NH4+] | Nc1ccc(OCc2nccs2)c(Cl)c1.Nc1ccccc1 | null | [Zn] | CO | Aromatic Heterocycle Formation | OtherReaction | 4b6ca6dfc21b7bd982d0ede5928d24946e8e2f3ee288707de9a59610254f11fa | 857e5eea1f59348bb4791b09731d4a604d098fda02b1b5db4c5acd91b2df8e04 | c1ccc(OCc2nccs2)cc1.c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4].[NH4+;D0:5]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8] | 397.9 | [{"value": 85.0, "product": "C1(=CC=CC=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 397.9, "product": "C1(=CC=CC=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 3-Chloro-4-(thiazol-2-ylmethoxy)-phenylamine is prepared by added Zn dust (55.9 g, 856 mmol) to a mixture of 2-(2-chloro-4-nitro-phenoxymethyl)-thiazole (47.0 g, 190 mmol) in 5:1 MeOH:saturated aqueous NH4Cl solution (600 ml). After 2 h, the reaction mixture is filtered, and the filtrate concentrated. The resulting sol... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine.Primary amine | null | c1ccccc1 | c1ccccc1.c1cscn1.c1ccccc1 | null | [Zn].CO | null | 2 | O=[N+]([O-])c1ccc(OCc2nccs2)c(Cl)c1.[NH4+]>[Zn].CO>Nc1ccc(OCc2nccs2)c(Cl)c1.Nc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9cbd597be3574ea3adaec85f4b538689 | COC(=O)Cl.NC1(C(=O)O)CCNCC1>>CNC1(CO)CCN(C)CC1 | ClC(=O)OC.Cl.Cl.NC1(CCNCC1)C(=O)O.CCN(CC)CC.Cl.Cl.NC1(CCNCC1)C(=O)O>>CN1CCC(CC1)(NC)CO | O=[C:1](Cl)O[CH3:9].O=[C:4]([C:3]1([NH2:2])[CH2:6][CH2:7][NH:8][CH2:10][CH2:11]1)[OH:5]>>[CH3:1][NH:2][C:3]1([CH2:4][OH:5])[CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][CH2:11]1 | COC(=O)Cl.NC1(C(=O)O)CCNCC1 | CNC1(CO)CCN(C)CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | e1e6b4a6b37d167303afb3ea054f89bd46e86a8fc4cd4ce6d0622a75407e0616 | f4a4a324c158ab8d122a9482ba782826b0d47ab2d6df9c484c76773ba8827cdb | C1CCNCC1 | Cl-[C;H0;D3;+0:1](=O)-O-[CH3;D1;+0:2].O=[C;H0;D3;+0:3](-[O;D1;H1:4])-[C:5]1(-[NH2;D1;+0:6])-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[CH3;D1;+0:1]-[NH;D2;+0:6]-[C:5]1(-[CH2;D2;+0:3]-[O;D1;H1:4])-[C:7]-[C:8]-[N;H0;D3;+0:9](-[CH3;D1;+0:2])-[C:10]-[C:11]-1 | null | [] | 0 | CELSIUS | 16 | HOUR | (1-Methyl-4-methylamino-piperidin-4-yl)-methanol is prepared from 4-amino-piperidine-4-carboxylic acid 2 HCl. Methyl chloroformate (0.40 g, 4.2 mmol) is added dropwise to a mixture of 4-amino-piperidine-4-carboxylic acid 2 HCl (0.278 g, 1.28 mmol) and Et3N (0.713 g, 7.04 mmol) in THF (10 ml) at room temperature. After ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Ether.Primary amine.Secondary amine | Primary alcohol.Secondary amine.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | Other | C1CCOC1 | 0 | 16 | COC(=O)Cl.NC1(C(=O)O)CCNCC1>C1CCOC1>CNC1(CO)CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e87d87f71e54514bdfad5cfe3fe54ae | Nc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1.OCC(O)CNCC(F)(F)F>>OCC1CN(CC(F)(F)F)C(=Nc2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)O1 | FC(CNCC(CO)O)(F)F.CCN=C=NCCCN(C)C.NC(=S)N.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC1=NC=NC2=CC=C(C=C12)N.CCN=C=NCCCN(C)C.C1=CN(C=N1)C(=S)N2C=CN=C2.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC1=NC=NC2=CC=C(C=C12)N>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC1=NC=NC2=CC=C(C=C12)N=C1OC(CN1CC(F)(F)F)CO | [NH2:12][c:13]1[cH:14][cH:15][c:16]2[n:17][cH:18][n:19][c:20]([NH:21][c:22]3[cH:23][cH:24][c:25]([O:26][CH2:27][c:28]4[cH:29][cH:30][cH:31][c:32]([F:33])[cH:34]4)[c:35]([Cl:36])[cH:37]3)[c:38]2[cH:39]1.[OH:1][CH2:2][CH:3]([CH2:4][NH:5][CH2:6][C:7]([F:8])([F:9])[F:10])[OH:40]>>[OH:1][CH2:2][CH:3]1[CH2:4][N:5]([CH2:6][C:... | Nc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1.OCC(O)CNCC(F)(F)F | OCC1CN(CC(F)(F)F)C(=Nc2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)O1 | null | CN(C)C=1C=CN=CC1 | O.ClCCCl.C1CCOC1 | Acylation | OtherReaction | 99c94d9cc813be842ea6bda362bd67bbf8a84107456b01d3b925d2deb9f96445 | 4fc4adf248e668e2e318ed81014ba921f8749fd17ea17248ba566a6b5c9f92bf | c1ccc(COc2ccc(Nc3ncnc4ccc(N=C5NCCO5)cc34)cc2)cc1 | [C:1]-[C:2](-[OH;D1;+0:3])-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:1]-[C:2]1-[C:4]-[N;H0;D3;+0:5](-[C:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10])-[C:15](=[N;H0;D2;+0:11]-[c:12](:[c:13]):[c:14])-[O;H0;D2;+0:3]-1 | null | [] | 70 | CELSIUS | 30 | MINUTE | [2-{4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-ylimino}-3-(2,2,2-trifluoro-ethyl)-oxazolidin-5-yl]-methanol is prepared from N4-[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-quinazoline-4,6-diamine. 1,1-Thiocarbonyldiimidazole (55 mg, 0.28 mmol) is added to a solution of N4-[3-chloro-4-(3-fluoro-benzyloxy)... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Primary amine.Secondary amine | Ether.Tertiary amine | null | C1COC[NH]1 | C1COC[NH]1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | Other | CN(C)C=1C=CN=CC1.O.ClCCCl.C1CCOC1 | 70 | 0.5 | Nc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1.OCC(O)CNCC(F)(F)F>CN(C)C=1C=CN=CC1.O.ClCCCl.C1CCOC1>OCC1CN(CC(F)(F)F)C(=Nc2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-300b23efc5df41b5afa4511337220cd7 | CN1CCCC1=O.Nc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1>>CN1CCCC1=Nc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1 | P(=O)(Cl)(Cl)Cl.CN1C(CCC1)=O.CCN(CC)CC.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC1=NC=NC2=CC=C(C=C12)N.CN1C(CCC1)=O.ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC1=NC=NC2=CC=C(C=C12)N>>ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC1=NC=NC2=CC=C(C=C12)N=C1N(CCC1)C | O=[C:6]1[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5]1.[NH2:7][c: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][CH2:22][c:23]4[cH:24][cH:25][cH:26][c:27]([F:28])[cH:29]4)[c:30]([Cl:31])[cH:32]3)[c:33]2[cH:34]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C:6]1=[N:7][c:8]1[cH:9][cH:10][c:11]2[n:... | CN1CCCC1=O.Nc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1 | CN1CCCC1=Nc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 51b0f3ede85ca5749ce72480877a1722a21fe77a78bc616c9927d9870542835e | b9d219f0674c4c56492b0e55f3afda0e6dc263a5614af120d7a27809c687708b | c1ccc(COc2ccc(Nc3ncnc4ccc(N=C5CCCN5)cc34)cc2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[#7:5]-1-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[#7:5]1-[C:4]-[C:3]-[C:2]-[C;H0;D3;+0:1]-1=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 8 | [{"value": 8.0, "product": "ClC=1C=C(C=CC1OCC1=CC(=CC=C1)F)NC1=NC=NC2=CC=C(C=C12)N=C1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | N4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenyl]-N6-(1-methyl-pyrrolidin-2-ylidene)-quinazoline-4,6-diamine is prepared by reacting N4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenyl]-quinazoline-4,6-diamine and 1-methyl-pyrrolidin-2-one. Phosphorous oxychloride (0.047 g, 0.30 mmol) is added to a stirred solution of 1-methyl-pyrrol... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine | null | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 0.166667 | CN1CCCC1=O.Nc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1>C(Cl)Cl>CN1CCCC1=Nc1ccc2ncnc(Nc3ccc(OCc4cccc(F)c4)c(Cl)c3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-686aba477f54414d8fe138645ccd7647 | ClCCNCCCl>>CN(CCCl)CCCl | C(=O)O.Cl.ClCCNCCCl>>Cl.ClCCN(CCCl)C | [NH:2]([CH2:3][CH2:4][Cl:5])[CH2:6][CH2:7][Cl:8]>>[CH3:1][N:2]([CH2:3][CH2:4][Cl:5])[CH2:6][CH2:7][Cl:8] | ClCCNCCCl | CN(CCCl)CCCl | null | null | C=O | Miscellaneous | OtherReaction | e82afbee4b71feacc35964d8bb2733f35366aa1a243f93701c51f5f60cd2769e | 06e4cfdff0e70e885199cc5de7382cc871277954ed1dd9750edc3ce3b12c44bd | null | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[C;D1;H3:6])-[C:4]-[C:5] | null | [] | null | null | null | null | Formic acid (10.0 g; 0.2 mol) and 37% formaldehyde (20 ml) were mixed in a 250 ml round-bottom flask equipped with reflux condenser. 1,5-Dichloro-3-azapentane, hydrochloride (17.0 g; 0.1 mol) was added and the solution was heated with magnetic stirring at 100 C. After 3 h the temperature was increased to 120 C for 20 m... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | null | null | null | Other | C=O | null | null | ClCCNCCCl>C=O>CN(CCCl)CCCl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4932d407f85c4531818eec34895cacb4 | Cc1ccc2ncncc2c1>>O=Cc1ccc2ncncc2c1 | CC=1C=C2C=NC=NC2=CC1.[Se](=O)=O>>N1=CN=CC2=CC(=CC=C12)C=O | [CH3:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][n:9][cH:10][c:11]2[cH:12]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][n:9][cH:10][c:11]2[cH:12]1 | Cc1ccc2ncncc2c1 | O=Cc1ccc2ncncc2c1 | null | null | CO | Oxidation | OtherReaction | f82793a7e1ee6561b7709c4a971f65b04fd777875bf3438ec6d6e1a0cf7ef2e4 | 4f1055c03ef3f74f7ecbf5450c9237f5c3ae016780958675e61943dfb81da1e6 | c1ccc2ncncc2c1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[O;D1;H0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 43.7 | [{"value": 43.7, "product": "N1=CN=CC2=CC(=CC=C12)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.7, "product": "N1=CN=CC2=CC(=CC=C12)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | The mixture of 6-methyl-quinazoline (5.0 g, 34.7 mmol) and selenium dioxide (7.7 g, 69.4 mmol) was heated at 160° C. for 12 hours. After cooling to room temperature, methanol was added with stirring. After removal of solid by filtration, the filtrate was concentrated. Flash chromatography (Merck Silica gel 60, 230-400 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | null | null | c1ccc2ncncc2c1 | Other | CO | 160 | null | Cc1ccc2ncncc2c1>CO>O=Cc1ccc2ncncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9eeb4f645e2c499f81ab7a4870eda4cf | O=C1CSC(=S)N1.O=Cc1ccc2ncncc2c1>>O=C1NC(=S)SC1=Cc1ccc2ncncc2c1 | O.N1=CN=CC2=CC(=CC=C12)C=O.S1C(=S)NC(=O)C1.C(C)(=O)[O-].[Na+]>>N1=CN=CC2=CC(=CC=C12)C=C1C(NC(S1)=S)=O | [O:1]=[C:2]1[NH:3][C:4](=[S:5])[S:6][CH2:7]1.O=[CH:8][c:9]1[cH:10][cH:11][c:12]2[n:13][cH:14][n:15][cH:16][c:17]2[cH:18]1>>[O:1]=[C:2]1[NH:3][C:4](=[S:5])[S:6][C:7]1=[CH:8][c:9]1[cH:10][cH:11][c:12]2[n:13][cH:14][n:15][cH:16][c:17]2[cH:18]1 | O=C1CSC(=S)N1.O=Cc1ccc2ncncc2c1 | O=C1NC(=S)SC1=Cc1ccc2ncncc2c1 | null | null | C(C)(=O)O | C-C Coupling | Aldol condensation | 9a823fd9b4e4348a3556e295dbe35eee5775ba89af420a0e94956549a8f5e1f0 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1NC(=S)SC1=Cc1ccc2ncncc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8](=[S;D1;H0:9])-[#16:10]-[CH2;D2;+0:11]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8](=[S;D1;H0:9])-[#16:10]-[C;H0;D3;+0:11]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 100.1 | [{"value": 100.0, "product": "N1=CN=CC2=CC(=CC=C12)C=C1C(NC(S1)=S)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.1, "product": "N1=CN=CC2=CC(=CC=C12)C=C1C(NC(S1)=S)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 12 | HOUR | The suspension of 6-quinazolinecarboxaldehyde (example 1a, 1.5 g, 9.5 mmol), rhodanine (1.26 g, 9.5 mmol) and sodium acetate (3.11 g, 38 mmol) in acetic acid (10 mL) was stirred at 130° C. for 12 h. After cooling to room temperature, water (40 mL) was added. The solid was collected by filtration, washed with water and ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | C1CSCN1.c1ccc2ncncc2c1 | HO- | C(C)(=O)O | 130 | 12 | O=C1CSC(=S)N1.O=Cc1ccc2ncncc2c1>C(C)(=O)O>O=C1NC(=S)SC1=Cc1ccc2ncncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc890660d1544bbab5e2ef2deedd13b9 | CI.O=C1NC(=S)SC1=Cc1ccc2ncncc2c1>>CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1 | O.N1=CN=CC2=CC(=CC=C12)C=C1C(NC(S1)=S)=O.IC.C(C)(C)N(CC)C(C)C>>CSC=1SC(C(N1)=O)=CC=1C=C2C=NC=NC2=CC1 | I[CH3:1].[S:2]=[C:3]1[NH:4][C:5](=[O:6])[C:7](=[CH:8][c:9]2[cH:10][cH:11][c:12]3[n:13][cH:14][n:15][cH:16][c:17]3[cH:18]2)[S:19]1>>[CH3:1][S:2][C:3]1=[N:4][C:5](=[O:6])[C:7](=[CH:8][c:9]2[cH:10][cH:11][c:12]3[n:13][cH:14][n:15][cH:16][c:17]3[cH:18]2)[S:19]1 | CI.O=C1NC(=S)SC1=Cc1ccc2ncncc2c1 | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1 | null | null | C(C)O | Protection | OtherReaction | 606299822d11e78b49ffccdb87ddf11b466a7927f0b837136809f8c27bf608bf | bbec82976efcb145836597f217d55880679ed600406b99e51babaa9ec4377cfd | O=C1N=CSC1=Cc1ccc2ncncc2c1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3]1-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[S;H0;D1;+0:6])-[#16:7]-[C:8]-1=[C:9]-[c:10]>>[CH3;D1;+0:1]-[S;H0;D2;+0:6]-[C;H0;D3;+0:5]1=[N;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[C:8](=[C:9]-[c:10])-[#16:7]-1 | 92 | [{"value": 92.0, "product": "CSC=1SC(C(N1)=O)=CC=1C=C2C=NC=NC2=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.4, "product": "CSC=1SC(C(N1)=O)=CC=1C=C2C=NC=NC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | The suspension of 5-quinazolin-6-ylmethylene-2-thioxo-thiazolidin-4-one (example 1b, 2.6 g, 9.52 mmol), iodomethane (1.2 mL, 19.0 mmol) and diisopropylethylamine (DIEA) (2.4 mL, 14.3 mmol) in anhydrous ethanol (100 mL) was stirred at room temperature for 12 h. After adding water (200 mL), the solid was collected by fil... | 10.6084/m9.figshare.5104873.v1 | null | Thioamide.Secondary amide.Monosulfide | Monosulfide.Monosulfide | C1CSCN1 | C1=NCCS1 | C1=NCCS1.c1ccc2ncncc2c1 | HI | C(C)O | null | 12 | CI.O=C1NC(=S)SC1=Cc1ccc2ncncc2c1>C(C)O>CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e584cb90a00450092165bd64b716562 | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.NCc1cccs1>>O=C1N=C(NCc2cccs2)S/C1=C\c1ccc2ncncc2c1 | CSC=1SC(C(N1)=O)=CC=1C=C2C=NC=NC2=CC1.S1C(=CC=C1)CN.C(C)(C)N(CC)C(C)C>>N1=CN=CC2=CC(=CC=C12)\C=C/1\C(N=C(S1)NCC=1SC=CC1)=O | CS[C:4]1=[N:3][C:2](=[O:1])[C:13](=[CH:14][c:15]2[cH:16][cH:17][c:18]3[n:19][cH:20][n:21][cH:22][c:23]3[cH:24]2)[S:12]1.[NH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][s:11]1>>[O:1]=[C:2]1[N:3]=[C:4]([NH:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][s:11]2)[S:12]/[C:13]1=[CH:14]\[c:15]1[cH:16][cH:17][c:18]2[n:19][cH:20][n:21][cH:22][c:23... | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.NCc1cccs1 | O=C1N=C(NCc2cccs2)S/C1=C\c1ccc2ncncc2c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 035918be13b9b18f90797b4193e038db335b9f8b189825e4bf2d79accb1614b7 | 323450ed6173b441dc292878481f00306cb335392bde193e8384a1208de2417f | O=C1N=C(NCc2cccs2)S/C1=C\c1ccc2ncncc2c1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6]-[c:7])-[#16:8]-1.[#16;a:9]:[c:10]-[C:11]-[NH2;D1;+0:12]>>[#16;a:9]:[c:10]-[C:11]-[NH;D2;+0:12]-[C;H0;D3;+0:1]1=[#7:2]-[C:3](=[O;D1;H0:4])/[C:5](=[C:6]/[c:7])-[#16:8]-1 | null | [] | 145 | CELSIUS | null | null | The suspension of 2-methylsulfanyl-5-quinazolin-6-ylmethylene-thiazol-4-one (example 1c, 58 mg, 0.2 mmol), thiophene methyl amine (45.3 mg, 0.4 mmol) and diisopropylethylamine (DIEA) (70 uL, 0.4 mmol) in acetonitrile (1 mL) was heated to 145° C. by microwave for 20 min. After cooling to room temperature, the solid was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide.Monosulfide | Secondary amine.Monosulfide | C1=NCCS1 | C1=NCCS1 | C1=NCCS1.c1ccsc1.c1ccc2ncncc2c1 | Other | C(C)#N | 145 | null | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.NCc1cccs1>C(C)#N>O=C1N=C(NCc2cccs2)S/C1=C\c1ccc2ncncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c1bc7c12f282409c8a90a8a2a9661ac0 | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.Nc1nccs1>>O=C1N=C(Nc2nccs2)S/C1=C\c1ccc2ncncc2c1 | CSC=1SC(C(N1)=O)=CC=1C=C2C=NC=NC2=CC1.S1C(=NC=C1)N.CCN(C(C)C)C(C)C>>N1=CN=CC2=CC(=CC=C12)\C=C/1\C(N=C(S1)NC=1SC=CN1)=O | CS[C:4]1=[N:3][C:2](=[O:1])[C:12](=[CH:13][c:14]2[cH:15][cH:16][c:17]3[n:18][cH:19][n:20][cH:21][c:22]3[cH:23]2)[S:11]1.[NH2:5][c:6]1[n:7][cH:8][cH:9][s:10]1>>[O:1]=[C:2]1[N:3]=[C:4]([NH:5][c:6]2[n:7][cH:8][cH:9][s:10]2)[S:11]/[C:12]1=[CH:13]\[c:14]1[cH:15][cH:16][c:17]2[n:18][cH:19][n:20][cH:21][c:22]2[cH:23]1 | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.Nc1nccs1 | O=C1N=C(Nc2nccs2)S/C1=C\c1ccc2ncncc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 035918be13b9b18f90797b4193e038db335b9f8b189825e4bf2d79accb1614b7 | 323450ed6173b441dc292878481f00306cb335392bde193e8384a1208de2417f | O=C1N=C(Nc2nccs2)S/C1=C\c1ccc2ncncc2c1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6]-[c:7])-[#16:8]-1.[NH2;D1;+0:9]-[c:10]1:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:1>>[O;D1;H0:4]=[C:3]1-[#7:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10]2:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:2)-[#16:8]/[C:5]-1=[C:6]\[c:7] | null | [] | null | null | null | null | Similar procedure as described in example 1d was used, starting from 2-methylsulfanyl-5-quinazolin-6-ylmethylene-thiazol-4-one, thiazol-2-ylamine and DIEA to give 5-[1-quinazolin-6-yl-meth-(Z)-ylidene]-2-(thiazol-2-ylamino)-thiazol-4-one: LC-MS m/e observed. LC-MS m/e 340 (MH+).
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide.Monosulfide | Secondary amine.Monosulfide | C1=NCCS1 | C1=NCCS1 | C1=NCCS1.c1cscn1.c1ccc2ncncc2c1 | Other | null | null | null | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.Nc1nccs1>>O=C1N=C(Nc2nccs2)S/C1=C\c1ccc2ncncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a6c05bedd6d4f8aa4c5e3f539bca68a | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.NCCc1cccc(F)c1>>O=C1N=C(NCCc2cccc(F)c2)S/C1=C\c1ccc2ncncc2c1 | CSC=1SC(C(N1)=O)=CC=1C=C2C=NC=NC2=CC1.FC=1C=C(C=CC1)CCN.CCN(C(C)C)C(C)C>>FC=1C=C(C=CC1)CCNC=1S\C(\C(N1)=O)=C/C=1C=C2C=NC=NC2=CC1 | CS[C:4]1=[N:3][C:2](=[O:1])[C:16](=[CH:17][c:18]2[cH:19][cH:20][c:21]3[n:22][cH:23][n:24][cH:25][c:26]3[cH:27]2)[S:15]1.[NH2:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([F:13])[cH:14]1>>[O:1]=[C:2]1[N:3]=[C:4]([NH:5][CH2:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[cH:14]2)[S:15]/[C:16]1=[CH:17]\[c:18]1[cH:19... | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.NCCc1cccc(F)c1 | O=C1N=C(NCCc2cccc(F)c2)S/C1=C\c1ccc2ncncc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 035918be13b9b18f90797b4193e038db335b9f8b189825e4bf2d79accb1614b7 | 323450ed6173b441dc292878481f00306cb335392bde193e8384a1208de2417f | O=C1N=C(NCCc2ccccc2)S/C1=C\c1ccc2ncncc2c1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6]-[c:7])-[#16:8]-1.[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1]1=[#7:2]-[C:3](=[O;D1;H0:4])/[C:5](=[C:6]/[c:7])-[#16:8]-1 | null | [] | null | null | null | null | Similar procedure as described in example 1d was used, starting from 2-methylsulfanyl-5-quinazolin-6-ylmethylene-thiazol-4-one, 2-(3-fluoro-phenyl)-ethylamine and DIEA to give 2-[2-(3-fluoro-phenyl)-ethylamino]-5-[1-quinazolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one: LC-MS m/e observed. LC-MS m/e 379 (MH+).
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide.Monosulfide | Secondary amine.Monosulfide | C1=NCCS1 | C1=NCCS1 | C1=NCCS1.c1ccccc1.c1ccc2ncncc2c1 | Other | null | null | null | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.NCCc1cccc(F)c1>>O=C1N=C(NCCc2cccc(F)c2)S/C1=C\c1ccc2ncncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89c120392ee84e0b89b32e9f07b48acb | CCOc1ccccc1N.CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1>>CCOc1ccccc1NC1=NC(=O)/C(=C/c2ccc3ncncc3c2)S1 | CSC=1SC(C(N1)=O)=CC=1C=C2C=NC=NC2=CC1.C(C)OC1=C(N)C=CC=C1.CCN(C(C)C)C(C)C>>C(C)OC1=C(C=CC=C1)NC=1S\C(\C(N1)=O)=C/C=1C=C2C=NC=NC2=CC1 | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[NH2:10].CS[C:11]1=[N:12][C:13](=[O:14])[C:15](=[CH:16][c:17]2[cH:18][cH:19][c:20]3[n:21][cH:22][n:23][cH:24][c:25]3[cH:26]2)[S:27]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[NH:10][C:11]1=[N:12][C:13](=[O:14])/[C:15](=[CH:16]/[c:17]2[cH:18][cH:19][c... | CCOc1ccccc1N.CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1 | CCOc1ccccc1NC1=NC(=O)/C(=C/c2ccc3ncncc3c2)S1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 035918be13b9b18f90797b4193e038db335b9f8b189825e4bf2d79accb1614b7 | 323450ed6173b441dc292878481f00306cb335392bde193e8384a1208de2417f | O=C1N=C(Nc2ccccc2)S/C1=C\c1ccc2ncncc2c1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6]-[c:7])-[#16:8]-1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:4]=[C:3]1-[#7:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[#16:8]/[C:5]-1=[C:6]\[c:7] | null | [] | null | null | null | null | Similar procedure as described in example 1d was used, starting from 2-methylsulfanyl-5-quinazolin-6-ylmethylene-thiazol-4-one, 2-ethoxyaniline and DIEA to give 2-(2-ethoxy-phenylamino)-5-[1-quinazolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one: LC-MS m/e observed. LC-MS m/e 377 (MH+).
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide.Monosulfide | Secondary amine.Monosulfide | C1=NCCS1 | C1=NCCS1 | c1ccccc1.C1=NCCS1.c1ccc2ncncc2c1 | Other | null | null | null | CCOc1ccccc1N.CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1>>CCOc1ccccc1NC1=NC(=O)/C(=C/c2ccc3ncncc3c2)S1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9c86364f61f844208660d6212207cf6f | COc1cc(F)ccc1N.CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1>>COc1cc(F)ccc1NC1=NC(=O)/C(=C/c2ccc3ncncc3c2)S1 | CSC=1SC(C(N1)=O)=CC=1C=C2C=NC=NC2=CC1.FC1=CC(=C(N)C=C1)OC.CCN(C(C)C)C(C)C>>FC1=CC(=C(C=C1)NC=1S\C(\C(N1)=O)=C/C=1C=C2C=NC=NC2=CC1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[NH2:10].CS[C:11]1=[N:12][C:13](=[O:14])[C:15](=[CH:16][c:17]2[cH:18][cH:19][c:20]3[n:21][cH:22][n:23][cH:24][c:25]3[cH:26]2)[S:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[NH:10][C:11]1=[N:12][C:13](=[O:14])/[C:15](=[CH:16]/[c:17]2[cH:18][cH:19][c:2... | COc1cc(F)ccc1N.CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1 | COc1cc(F)ccc1NC1=NC(=O)/C(=C/c2ccc3ncncc3c2)S1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 035918be13b9b18f90797b4193e038db335b9f8b189825e4bf2d79accb1614b7 | 323450ed6173b441dc292878481f00306cb335392bde193e8384a1208de2417f | O=C1N=C(Nc2ccccc2)S/C1=C\c1ccc2ncncc2c1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6]-[c:7])-[#16:8]-1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:4]=[C:3]1-[#7:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[#16:8]/[C:5]-1=[C:6]\[c:7] | null | [] | null | null | null | null | Similar procedure as described in example 1d was used, starting from 2-methylsulfanyl-5-quinazolin-6-ylmethylene-thiazol-4-one, 4-fluoro-2-methoxy-aniline and DIEA to give 2-(4-fluoro-2-methoxy-phenylamino)-5-[1-quinazolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one: LC-MS m/e observed. LC-MS m/e 381 (MH+).
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide.Monosulfide | Secondary amine.Monosulfide | C1=NCCS1 | C1=NCCS1 | c1ccccc1.C1=NCCS1.c1ccc2ncncc2c1 | Other | null | null | null | COc1cc(F)ccc1N.CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1>>COc1cc(F)ccc1NC1=NC(=O)/C(=C/c2ccc3ncncc3c2)S1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d6657e347a6b4e529294c0b83410d5fe | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.Nc1cccc(F)c1>>O=C1N=C(Nc2cccc(F)c2)S/C1=C\c1ccc2ncncc2c1 | CSC=1SC(C(N1)=O)=CC=1C=C2C=NC=NC2=CC1.FC=1C=C(N)C=CC1.CCN(C(C)C)C(C)C>>FC=1C=C(C=CC1)NC=1S\C(\C(N1)=O)=C/C=1C=C2C=NC=NC2=CC1 | CS[C:4]1=[N:3][C:2](=[O:1])[C:14](=[CH:15][c:16]2[cH:17][cH:18][c:19]3[n:20][cH:21][n:22][cH:23][c:24]3[cH:25]2)[S:13]1.[NH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([F:11])[cH:12]1>>[O:1]=[C:2]1[N:3]=[C:4]([NH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([F:11])[cH:12]2)[S:13]/[C:14]1=[CH:15]\[c:16]1[cH:17][cH:18][c:19]2[n:20][cH:21][n:2... | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.Nc1cccc(F)c1 | O=C1N=C(Nc2cccc(F)c2)S/C1=C\c1ccc2ncncc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 035918be13b9b18f90797b4193e038db335b9f8b189825e4bf2d79accb1614b7 | 323450ed6173b441dc292878481f00306cb335392bde193e8384a1208de2417f | O=C1N=C(Nc2ccccc2)S/C1=C\c1ccc2ncncc2c1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6]-[c:7])-[#16:8]-1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:4]=[C:3]1-[#7:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[#16:8]/[C:5]-1=[C:6]\[c:7] | null | [] | null | null | null | null | Similar procedure as described in example 1d was used, starting from 2-methylsulfanyl-5-quinazolin-6-ylmethylene-thiazol-4-one, 3-fluoroaniline and DIEA to give 2-(3-fluoro-phenylamino)-5-[1-quinazolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one: LC-MS m/e observed. LC-MS m/e 351 (MH+).
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide.Monosulfide | Secondary amine.Monosulfide | C1=NCCS1 | C1=NCCS1 | C1=NCCS1.c1ccccc1.c1ccc2ncncc2c1 | Other | null | null | null | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.Nc1cccc(F)c1>>O=C1N=C(Nc2cccc(F)c2)S/C1=C\c1ccc2ncncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-57163b1f79a04964992eba5ffa026e39 | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.NCc1cccc(F)c1>>O=C1N=C(NCc2cccc(F)c2)S/C1=C\c1ccc2ncncc2c1 | CSC=1SC(C(N1)=O)=CC=1C=C2C=NC=NC2=CC1.FC=1C=C(CN)C=CC1.CCN(C(C)C)C(C)C>>FC=1C=C(CNC=2S\C(\C(N2)=O)=C/C=2C=C3C=NC=NC3=CC2)C=CC1 | CS[C:4]1=[N:3][C:2](=[O:1])[C:15](=[CH:16][c:17]2[cH:18][cH:19][c:20]3[n:21][cH:22][n:23][cH:24][c:25]3[cH:26]2)[S:14]1.[NH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]1>>[O:1]=[C:2]1[N:3]=[C:4]([NH:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]2)[S:14]/[C:15]1=[CH:16]\[c:17]1[cH:18][cH:19][c:20]2[... | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.NCc1cccc(F)c1 | O=C1N=C(NCc2cccc(F)c2)S/C1=C\c1ccc2ncncc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 035918be13b9b18f90797b4193e038db335b9f8b189825e4bf2d79accb1614b7 | 323450ed6173b441dc292878481f00306cb335392bde193e8384a1208de2417f | O=C1N=C(NCc2ccccc2)S/C1=C\c1ccc2ncncc2c1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6]-[c:7])-[#16:8]-1.[NH2;D1;+0:9]-[C:10]-[c:11]>>[O;D1;H0:4]=[C:3]1-[#7:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[C:10]-[c:11])-[#16:8]/[C:5]-1=[C:6]\[c:7] | null | [] | null | null | null | null | Similar procedure as described in example 1d was used, starting from 2-methylsulfanyl-5-quinazolin-6-ylmethylene-thiazol-4-one, 3-fluoro-benzylamine and DIEA to give 2-(3-fluoro-benzylamino)-5-[1-quinazolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one: LC-MS m/e observed. LC-MS m/e 379 (MH+).
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide.Monosulfide | Secondary amine.Monosulfide | C1=NCCS1 | C1=NCCS1 | C1=NCCS1.c1ccccc1.c1ccc2ncncc2c1 | Other | null | null | null | CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1.NCc1cccc(F)c1>>O=C1N=C(NCc2cccc(F)c2)S/C1=C\c1ccc2ncncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3119269796b14e2ebfff7ec9656a3dfe | COc1ccc(N)c(OC)c1.CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1>>COc1ccc(NC2=NC(=O)/C(=C/c3ccc4ncncc4c3)S2)c(OC)c1 | CSC=1SC(C(N1)=O)=CC=1C=C2C=NC=NC2=CC1.COC1=C(C=CC(=C1)OC)N.CCN(C(C)C)C(C)C>>COC1=C(C=CC(=C1)OC)NC=1S\C(\C(N1)=O)=C/C=1C=C2C=NC=NC2=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:25]([O:26][CH3:27])[cH:28]1.CS[C:8]1=[N:9][C:10](=[O:11])[C:12](=[CH:13][c:14]2[cH:15][cH:16][c:17]3[n:18][cH:19][n:20][cH:21][c:22]3[cH:23]2)[S:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8]2=[N:9][C:10](=[O:11])/[C:12](=[CH:13]/[c:14]3[cH:15][cH:16][c:17]4[n:18][c... | COc1ccc(N)c(OC)c1.CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1 | COc1ccc(NC2=NC(=O)/C(=C/c3ccc4ncncc4c3)S2)c(OC)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 035918be13b9b18f90797b4193e038db335b9f8b189825e4bf2d79accb1614b7 | 323450ed6173b441dc292878481f00306cb335392bde193e8384a1208de2417f | O=C1N=C(Nc2ccccc2)S/C1=C\c1ccc2ncncc2c1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6]-[c:7])-[#16:8]-1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:4]=[C:3]1-[#7:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[#16:8]/[C:5]-1=[C:6]\[c:7] | null | [] | null | null | null | null | Similar procedure as described in example 1d was used, starting from 2-methylsulfanyl-5-quinazolin-6-ylmethylene-thiazol-4-one, 2,4-dimethoxy-phenylamine and DIEA to give 2-(2,4-dimethoxy-phenylamino)-5-[1-quinazolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one: LC-MS m/e observed. LC-MS m/e 393 (MH+).
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide.Monosulfide | Secondary amine.Monosulfide | C1=NCCS1 | C1=NCCS1 | c1ccccc1.C1=NCCS1.c1ccc2ncncc2c1 | Other | null | null | null | COc1ccc(N)c(OC)c1.CSC1=NC(=O)C(=Cc2ccc3ncncc3c2)S1>>COc1ccc(NC2=NC(=O)/C(=C/c3ccc4ncncc4c3)S2)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95da9d0afaa44711bde8cfef46cdfe2c | CC[O-].Clc1ncnc2ccc(Br)cc12>>CCOc1ncnc2ccc(Br)cc12 | BrC=1C=C2C(=NC=NC2=CC1)Cl.[O-]CC.[Na+]>>BrC=1C=C2C(=NC=NC2=CC1)OCC | [CH3:1][CH2:2][O-:3].Cl[c:4]1[n:5][cH:6][n:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]12>>[CH3:1][CH2:2][O:3][c:4]1[n:5][cH:6][n:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]12 | CC[O-].Clc1ncnc2ccc(Br)cc12 | CCOc1ncnc2ccc(Br)cc12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | b3369511118a10d7d701b55617dec1e99d233682c3e2c9839106d2edd5e7154d | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1ccc2ncncc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[C;D1;H3:9]-[C:10]-[O-;H0;D1:11]>>[C;D1;H3:9]-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8] | 55 | [{"value": 55.0, "product": "BrC=1C=C2C(=NC=NC2=CC1)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.1, "product": "BrC=1C=C2C(=NC=NC2=CC1)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | The suspension of 6-bromo-4-chloro-quinazoline (4.87 g, 20 mmol), sodium ethoxide (95%, 14.32 g, 200 mmol) in anhydrous ethyl alcohol (150 ml) was stirred at room temperature for 4 hr. After the reaction, solvent was evaporated. Then, ice water was added, followed by addition of 3 N HCL aq to adjust the pH to 9, and pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | Other | C(C)O | null | 4 | CC[O-].Clc1ncnc2ccc(Br)cc12>C(C)O>CCOc1ncnc2ccc(Br)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f77a56980c514bce8ba192b20d4f3644 | CCOc1ncnc2ccc(Br)cc12.[C]=O>>CCOc1ncnc2ccc(C=O)cc12 | [C]=O.BrC=1C=C2C(=NC=NC2=CC1)OCC.C1(=CC=CC=C1)C(CCP)C1=CC=CC=C1.C(C)N(CC)CC.[C]=O.C(CCCCC)[SiH](CCCCCC)CCCCCC.[C]=O>>C(C)OC1=NC=NC2=CC=C(C=C12)C=O | Br[c:11]1[cH:10][cH:9][c:8]2[n:7][cH:6][n:5][c:4]([O:3][CH2:2][CH3:1])[c:15]2[cH:14]1.[C:12]=[O:13]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][cH:6][n:7][c:8]2[cH:9][cH:10][c:11]([CH:12]=[O:13])[cH:14][c:15]12 | CCOc1ncnc2ccc(Br)cc12.[C]=O | CCOc1ncnc2ccc(C=O)cc12 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | ClCCl.CCCCCC.CN(C=O)C.C(C)(=O)OCC | C-C Coupling | OtherReaction | 7e500dcb6a15506506760c0b91f2be3c9354986602914d352ae22b475dbe8cab | e105999fc3261af8a4ba9409cf40c3a008ac3001c73ecaa65b53888846d190d1 | c1ccc2ncncc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:1):[c:8]:[#7;a:9].[C;H0;D1;+0:10]=[O;D1;H0:11]>>[#7;a:9]:[c:8]:[c:6]1:[c:7]:[c;H0;D3;+0:1](-[CH;D2;+0:10]=[O;D1;H0:11]):[c:2]:[c:3]:[c:4]:1:[#7;a:5] | 66 | [{"value": 66.0, "product": "C(C)OC1=NC=NC2=CC=C(C=C12)C=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | The mixture of 6-bromo-4-ethoxy-quinazoline (example 10a, 506 mg, 2 mmol,), diphenylpropyl phosphine (45.6 mg, 0.2 mmol), palladium acetate (44.8 mg, 0.2 mmol) and triethyl amine (505 mg, 5 mmol) in anhydrous N,N-dimethylformamide (DMF) (25 ml) was charged with carbon monoxide at 75 psi. After the above reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aldehyde | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | Br- | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].ClCCl.CCCCCC.CN(C=O)C.C(C)(=O)OCC | null | 0.25 | CCOc1ncnc2ccc(Br)cc12.[C]=O>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].ClCCl.CCCCCC.CN(C=O)C.C(C)(=O)OCC>CCOc1ncnc2ccc(C=O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a064e605354a4749a7c70a6ec0f0ce32 | CCNc1cccc(F)c1.O=C1CSC(=S)N1>>CCN(C1=NC(=O)CS1)c1cccc(F)c1 | FC=1C=C(C=CC1)NCC.S1C(=S)NC(=O)C1.CCN(C(C)C)C(C)C>>FC=1C=C(C=CC1)N(C=1SCC(N1)=O)CC | [CH3:1][CH2:2][NH:3][c:10]1[cH:11][cH:12][cH:13][c:14]([F:15])[cH:16]1.S=[C:4]1[NH:5][C:6](=[O:7])[CH2:8][S:9]1>>[CH3:1][CH2:2][N:3]([C:4]1=[N:5][C:6](=[O:7])[CH2:8][S:9]1)[c:10]1[cH:11][cH:12][cH:13][c:14]([F:15])[cH:16]1 | CCNc1cccc(F)c1.O=C1CSC(=S)N1 | CCN(C1=NC(=O)CS1)c1cccc(F)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 98557597263edf8660b42e956870f021155e688897cf851ed13564bfe96cab66 | 362fd90e8614394636bc0078179c3580fc41036508e6943430dbb1fff2ff1014 | O=C1CSC(Nc2ccccc2)=N1 | S=[C;H0;D3;+0:1]1-[#16:2]-[C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-1.[C;D1;H3:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1]1=[N;H0;D2;+0:6]-[C:4](=[O;D1;H0:5])-[C:3]-[#16:2]-1)-[c:10](:[c:11]):[c:12] | 76.6 | [{"value": 76.6, "product": "FC=1C=C(C=CC1)N(C=1SCC(N1)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.6, "product": "FC=1C=C(C=CC1)N(C=1SCC(N1)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | DAY | To a solution of (3-fluorophenyl)-ethylamine (3.06 g, 22 mmol) and rhodanine (2.66 g, 20 mmol) in acetonitrile (70 mL) was added DIEA (7.66 mL, 44 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (5.97 g, 22 mmol) was added in two portions. After addition, the suspension was allo... | 10.6084/m9.figshare.5104873.v1 | null | Thioamide.Secondary amide.Secondary amine | Tertiary amine.Monosulfide | C1CSCN1 | C1=NCCS1 | C1=NCCS1.c1ccccc1 | Other | C(C)#N | 0 | 72 | CCNc1cccc(F)c1.O=C1CSC(=S)N1>C(C)#N>CCN(C1=NC(=O)CS1)c1cccc(F)c1 |
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