p-Bromophenethylamine → [2-(4-Bromo-phenyl)-ethyl]-(4-{3-[(3(S)-methyl-piperidin-4(R)-ylamino)-methyl]-phenyl}-pyrimidin-2-yl)-amine

HRID 14940Notes

Reaction equation

HRID 14940 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[CH:29][N:28]=[C:27](Cl)[N:26]=3)[CH:20]=2)[C@@H:13]([CH3:32])[CH2:12]1)=O)C1C=CC=CC=1.[Br:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][NH2:42])=[CH:36][CH:35]=1>>[Br:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][NH:42][C:27]2[N:26]=[C:25]([C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([CH2:18][NH:17][C@@H:14]4[CH2:15][CH2:16][NH:11][CH2:12][C@@H:13]4[CH3:32])[CH:20]=3)[CH:30]=[CH:29][N:28]=2)=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 533915p-BromophenethylamineHCID 866033194(R)-[3-(2-Chloro-pyrimidin-4-yl)-benzylamino]-3(S)-methyl-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 58603604[2-(4-Bromo-phenyl)-ethyl]-(4-{3-[(3(S)-methyl-piperidin-4(R)-ylamino)-methyl]-phenyl}-pyrimidin-2-yl)-amine

Procedure

Intermediate 136 was coupled with 2-(4-bromo-phenyl)-ethylamine following procedure F. The resulting product was deprotected following procedure G3. LC-MS showed the product had the expected M+H+ of 481. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.67 (s, 1H) 8.39 (d, 2H) 7.95 (d, 1H)) 7.69 (t, 1H) 7.40 (d, 2H) 7.28 (d, 2H) 4.50 (s, 2H) 4.00 (m, 1H) 3.84 (m, 1H) 3.72 (m, 1H) 3.57 (m, 1H) 3.42 (d, 1H) 3.36 (d, 1H) 3.20 (t, 2H) 3.04 (t, 2H) 2.30 (m, 2H) 1.30 (d, 3H).

Sources & evidence

ORD record
ord-ca8c246a4a274acd8c5d5e7eff49fc73
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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