4-(2-Aminoethyl)-2,6-dichlorophenol → 2,6-Dichloro-4-(2-{4-[3-(piperidin-4-ylamino)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

HRID 14739Notes

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]=[C:35]([Cl:37])[C:34]([OH:38])=[C:33]([Cl:39])[CH:32]=1>>[Cl:37][C:35]1[CH:36]=[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:32]=[C:33]([Cl:39])[C:34]=1[OH:38]

Participants

Reactant 2

HCID 230715934-(2-Aminoethyl)-2,6-dichlorophenol

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

Product 1

HCID 586034522,6-Dichloro-4-(2-{4-[3-(piperidin-4-ylamino)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

Procedure

Intermediate 7 was coupled with 4-(2-Amino-ethyl)-2,6-dichloro-phenol following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 458. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.2 (d, 1H) 7.05-7.6 (m, 6H) 7.0 (m, 1H) 4.95 (m, 1H) 3.6-4.0 (m, 3H) 3.4 (m, 2H) 3.1-3.2 (m, 2H) 2.8-2.95 (m, 2H) 2.25 (m, 3H) 1.7 (m, 2H).

Sources & evidence

ORD record: ord-851dd43435854646a5c72dfe243830a6
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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