4-(2-Aminoethyl)-2-bromophenol → 2-Bromo-4-(2-{4-[3-(piperidin-4-ylamino)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

HRID 14741Notes

Reaction equation

HRID 14741 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][N:24]=[C:23](Cl)[N:22]=3)[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[NH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([Br:38])[CH:32]=1>>[Br:38][C:33]1[CH:32]=[C:31]([CH2:30][CH2:29][NH:28][C:23]2[N:22]=[C:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([NH:14][CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH:16]=3)[CH:26]=[CH:25][N:24]=2)[CH:36]=[CH:35][C:34]=1[OH:37]

Participants

3

Reactant 2

HCID 53238424-(2-Aminoethyl)-2-bromophenolHCID 866032444-[3-(2-Chloro-pyrimidin-4-yl)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 593410282-Bromo-4-(2-{4-[3-(piperidin-4-ylamino)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

Procedure

Intermediate 7 was coupled with 4-(2-Amino-ethyl)-2-bromo-phenol following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 468. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.8 (m, 5H) 8.4 (d, 1H) 7.4 (m, 2H) 7.3 (m, 1H) 7.0 (d, 1H) 6.9 (m, 1H) 3.7 (m, 2H) 3.4 (m, 1H) 3.1 (m, 2H) 2.9 (m, 3H) 2.1 (m, 1H) 1.8 (m, 2H) 1.5 (m, 2H).

Sources & evidence

ORD record
ord-13d63e428c524a0890588419ee5b3017
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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