3-Chloro-1H-indole-6-carboxylic acid → 4-{2-[(3-Chloro-1H-indole-6-carbonyl)amino]-2-(2-pyridinyl)-ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester

HRID 32407Notes

Reaction equation

HRID 32407 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][CH2:16][CH:17]([NH2:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:25][C:26]1[C:34]2[C:29](=[CH:30][C:31]([C:35](O)=[O:36])=[CH:32][CH:33]=2)[NH:28][CH:27]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][CH2:16][CH:17]([NH:24][C:35]([C:31]2[CH:30]=[C:29]3[C:34]([C:26]([Cl:25])=[CH:27][NH:28]3)=[CH:33][CH:32]=2)=[O:36])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 155430423-Chloro-1H-indole-6-carboxylic acidHCID 693132324-[2-Amino-2-(2-pyridinyl)-ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 693096804-{2-[(3-Chloro-1H-indole-6-carbonyl)amino]-2-(2-pyridinyl)-ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester

Procedure

Using coupling method A, 4-[2-amino-2-(2-pyridinyl)-ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester (730 mg, 2.2 mmol) and 3-chloroindole-6-carboxylic acid (468 mg, 2.4 mmol) afforded, after purification (SiO2: 10 DCM:2 EtOAc:2 Hexane:0 to 1.5 isopropyl amine), 835 mg (64%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 10 DCM:2 EtOAc:2 Hexane:0 to 1.5 isopropyl amine), 835 mg (64%) of the title compound

Sources & evidence

ORD record
ord-346106756f7f41f3bc0a8290500aee09
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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