2-(1H-Indol-5-yl)ethan-1-amine → (4-{3-[(Ethyl-piperidin-4-yl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-[2-(1H-indol-5-yl)-ethyl]-amine

HRID 14924Notes

Reaction equation

HRID 14924 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[CH:29]=[CH:28][N:27]=[C:26](Cl)[N:25]=3)[CH:19]=2)[CH2:15][CH3:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[NH:31]1[C:39]2[C:34](=[CH:35][C:36]([CH2:40][CH2:41][NH2:42])=[CH:37][CH:38]=2)[CH:33]=[CH:32]1>>[CH2:15]([N:14]([CH2:17][C:18]1[CH:19]=[C:20]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:42][CH2:41][CH2:40][C:36]3[CH:35]=[C:34]4[C:39](=[CH:38][CH:37]=3)[NH:31][CH:32]=[CH:33]4)[N:25]=2)[CH:21]=[CH:22][CH:23]=1)[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH3:16]

Participants

3

Reactant 2

HCID 172211022-(1H-Indol-5-yl)ethan-1-amine2×HCID 866032904-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-piperidine-1-carboxylic acid tert-butyl ester2×

Product 1

HCID 58603633(4-{3-[(Ethyl-piperidin-4-yl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-[2-(1H-indol-5-yl)-ethyl]-amine

Procedure

4-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-piperidine-1-carboxylic acid tert-butyl ester (intermediate 84) was coupled with 2-(1H-indol-5-yl)-ethylamine (intermediate 124) following procedure F then deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 455. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.31 ppm) δ 8.7 (m, 1H) 8.4 (m, 3H) 7.9 (m, 1H) 7.6 (m, 4H) 7.4 (m, 1H) 7.2 (m, 1H) 4.4 (m, 1H) 3.9 (m, 2H) 3.7 (m, 7H) 3.2 (m, 3H) 2.5 (m, 2H) 2.3 (m, 2H) 1.3 (m, 3H).

Sources & evidence

ORD record
ord-ebd2f1321062494ea9637761faec1d38
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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