1-Hydroxybenzotriazole → N-[6-(Pyrrolidin-1-yl)pyridin-3-yl]-5-iodo-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

HRID 1948800Notes

Reaction equation

HRID 1948800 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19]([OH:21])=O)=[CH:5]2.[NH2:22][C:23]1[CH:24]=[N:25][C:26]([N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:27][CH:28]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[N:29]1([C:26]2[N:25]=[CH:24][C:23]([NH:22][C:19]([C:6]3[N:7]([CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=4)[C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([I:1])=[CH:10][CH:9]=4)=[O:21])=[CH:28][CH:27]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 38991726-(Pyrrolidin-1-yl)pyridin-3-amineHCID 668504425-iodo-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylic acid

Product 1

HCID 66850279N-[6-(Pyrrolidin-1-yl)pyridin-3-yl]-5-iodo-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamideYield 70.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound was prepared according to a process similar to that described in stage 5.4, by reacting 0.3 g (0.76 mmol) of 5-iodo-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylic acid, prepared according to the protocol described in stage 8.2, with 148 mg (0.91 mmol) of 3-amino-6-(pyrrolidin-1-yl)pyridine in the presence of 145 mg (0.76 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDAC) and of 105 mg (0.76 mmol) of 1-hydroxybenzotriazole (HOBT) in 5 ml of dimethylformamide. 290 mg of the expected product are obtained.

Workup

  1. customThe compound was prepared
  2. customprepared

Sources & evidence

ORD record
ord-34627bda4b3a4f4aa8a70fb86d713a65
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

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