4-(2-Aminoethyl)-2-chlorophenol → 2-Chloro-4-(2-{4-[3-(2-piperidin-4-yl-ethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

HRID 14875Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][N:25]=[C:24](Cl)[N:23]=3)[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[NH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([Cl:39])[CH:33]=1>>[Cl:39][C:34]1[CH:33]=[C:32]([CH2:31][CH2:30][NH:29][C:24]2[N:23]=[C:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][CH2:14][CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH:17]=3)[CH:27]=[CH:26][N:25]=2)[CH:37]=[CH:36][C:35]=1[OH:38]

Participants

Reactant 2

HCID 230715554-(2-Aminoethyl)-2-chlorophenol

HCID 866032964-{2-[3-(2-Chloro-pyrimidin-4-yl)-phenyl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 586034872-Chloro-4-(2-{4-[3-(2-piperidin-4-yl-ethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

Procedure

Intermediate 94 was coupled with 4-(2-amino-ethyl)-2-chloro-phenol following procedure Q. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 437. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.27 (d, 1H), 8.05 (s, 1H), 7.99 (m, 1H), 7.46 (d, 2H), 7.35 (d, 1H), 7.24 (d, 1H), 7.03 (d, 1H), 6.80 (d, 1H), 3.70 (m, 2H), 3.35 (m, 2H), 2.78 (m, 6H), 1.99 (d, 2H), 1.66 (m, 3H), 1.37 (m, 2H).

Sources & evidence

ORD record: ord-263f315ba0954cf7b1b3cdcc85a570a8
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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