1,2-Dichloroethane → N-[(3R)-1-phenylpiperidin-3-yl]-3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

HRID 1467311Notes

Reaction equation

HRID 1467311 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]([OH:18])=O)[CH:14]=3)[N:9]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:8]=2)=[CH:3][CH:2]=1.[C:38]1([N:44]2[CH2:49][CH2:48][CH2:47][C@@H:46]([NH2:50])[CH2:45]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:38]1([N:44]2[CH2:49][CH2:48][CH2:47][C@@H:46]([NH:50][C:16]([C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[N:9]([C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:8]=[C:7]4[C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[O:18])[CH2:45]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 679963353-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylic acidHCID 70652306(3R)-1-phenylpiperidin-3-amine

Product 1

HCID 67995889N-[(3R)-1-phenylpiperidin-3-yl]-3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acid (97 mg, 0.20 mmol), (3R)-1-phenylpiperidin-3-amine (120 mg, 0.48 mmol), EDC (0.08 g, 0.4 mmol), HOBt (0.07 g, 0.5 mmol) and DIPEA (400 μl, 2.3 mmol) in DMF (2 ml) was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated in vacuo to provide crude N-[(3R)-1-phenylpiperidin-3-yl]-3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide, which was used as-is without further purification. LCMS calc'd for C43H38N5O [M+H]+=640; found 640.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f60b702a3cbb4d538298131e332d0a43
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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