1-Methylpiperidine-4-carboxylic acid → 1-Methyl-piperidine-4-carboxylic acid (3-{2-[2-(3-chloro-4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-isopropyl-amide

HRID 14922

Reaction equation

HRID 14922 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH:24][CH:25]([CH3:27])[CH3:26])[CH:18]=3)[CH:14]=[CH:13][N:12]=2)[CH:5]=[CH:4][C:3]=1[OH:28].[CH3:29][N:30]1[CH2:35][CH2:34][CH:33]([C:36](O)=[O:37])[CH2:32][CH2:31]1>>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=3)[CH2:23][N:24]([CH:25]([CH3:26])[CH3:27])[C:36]([CH:33]3[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]3)=[O:37])[CH:14]=[CH:13][N:12]=2)[CH:5]=[CH:4][C:3]=1[OH:28]

Participants

3

Reactant 2

HCID 27369391-Methylpiperidine-4-carboxylic acidHCID 586034412-Chloro-4-(2-{4-[3-(isopropylamino-methyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol2×

Product 1

HCID 586033921-Methyl-piperidine-4-carboxylic acid (3-{2-[2-(3-chloro-4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-isopropyl-amide

Procedure

2-Chloro-4-(2-{4-[3-(isopropylamino-methyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol (compound 132) was coupled with 1-methyl-piperidine-4-carboxylic acid following procedure D2. LC-MS showed the product had the expected M+H+ of 522. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.6 (s, 1H) 8.3 (m, 1H) 7.8 (m, 2H) 7.4 (m, 1H) 7.2 (s, 1H) 6.9 (m, 3H) 5.0 (s, br, 1H) 4.8 (m, 1H) 4.5 (d, 2H) 4.2 (m, 1H) 3.7 (m, 2H) 3.4 (s, 1H) 3.2 (m, 2H) 2.8 (m, 2H 2.5 (m, 5H) 2.0 (s, br, 2H) 1.9 (s, br, 1H) 1.2 (d, 3H) 1.0 (d, 3H).

Sources & evidence

ORD record
ord-1d11323bb6ee4de4abd029236a8cdbcb
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

Loading…