Propanal → 2-Chloro-4-{2-[4-(3-{[ethyl-(1-propyl-piperidin-4-yl)-amino]-methyl}-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

HRID 14864Notes

Reaction equation

HRID 14864 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][N:24]([CH2:31][CH3:32])[CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[CH:18]=3)[CH:14]=[CH:13][N:12]=2)[CH:5]=[CH:4][C:3]=1[OH:33].[CH:34](=O)[CH2:35][CH3:36]>>[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][N:24]([CH2:31][CH3:32])[CH:25]4[CH2:30][CH2:29][N:28]([CH2:34][CH2:35][CH3:36])[CH2:27][CH2:26]4)[CH:18]=3)[CH:14]=[CH:13][N:12]=2)[CH:5]=[CH:4][C:3]=1[OH:33]

Participants

3

Reactant 2

HCID 527PropanalHCID 586034392-Chloro-4-[2-(4-{3-[(ethyl-piperidin-4-yl-amino)-methyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol

Product 1

HCID 586037692-Chloro-4-{2-[4-(3-{[ethyl-(1-propyl-piperidin-4-yl)-amino]-methyl}-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

Procedure

Intermediate 85 was coupled with propionaldehyde following procedure E. The product was purified by HPLC. LC-MS showed the product had the expected M+H+ of 508. 1H NMR (Varian 300 MHz, DMSO, shifts relative to the solvent peak at 2.50 ppm) δ 8.3 (d, 1H), 7.9 (d, 1H), 7.5-7.4 (m, 3H), 7.2 (d, 1H), 7.1 (d, 1H), 7.0 (d, 1H), 6.8 (d, 1H), 3.6 (s, 2H), 3.5 (d, 2H), 3.1 (d, 2H), 2.7 (q, 2H), 2.6 (m, 3H), 2.3 (m, 4H), 1.7-1.6 (m, 4H), 1.5-1.4 (m, 2H), 0.94 (t, 3H), 0.80 (t, 3H).

Workup

  1. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-faa7df075dea40b8aee8e7083a91fa9d
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

Loading…