1-Hydroxybenzotriazole → Tert-butyl 4-(4-(2-amino-3-carbamoyl-5-chlorophenylcarbamoyl)phenyl)piperidine-1-carboxylate

HRID 2366473Notes

Reaction equation

HRID 2366473 reaction equation
[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:13]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1)(O)=[O:14].ON1C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:4](=[O:5])[NH2:6])=[CH:7][C:8]([Cl:12])=[CH:9][C:10]=1[NH:11][C:13]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]2)=[CH:18][CH:17]=1)=[O:14]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 224928594-(4-Carboxy-phenyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 251933212,3-Diamino-5-chlorobenzamide

Product 1

HCID 69262008Tert-butyl 4-(4-(2-amino-3-carbamoyl-5-chlorophenylcarbamoyl)phenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,3-diamino-5-chlorobenzamide (0.75 g), tert-butyl 4-(4-carboxyphenyl)-piperidine-1-carboxylate (0.17 g), 1-hydroxybenzotriazole (HOBT, 0.22 g), benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP, 0.85 g) and diisopropylethylamine (DIPEA, 0.85 mL) in DMF (5 mL) was stirred for 18 hours and concentrated. The concentrate was flash chromatographed on silica gel with 10% methanol/dichloromethane.

Workup

  1. concentrationconcentrated
  2. customchromatographed on silica gel with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-b9c72a8731d04d1187653ff678e71c99
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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