Dimethylamine → 4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-1-[1-(2-dimethylamino-pyrimidin-4-yl)-piperidin-4-ylmethyl]-piperazin-2-one

HRID 1433092Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-1-[1-(2-chloro-pyrimidin-4-yl)-piperidin-4-ylmethyl]-piperazin-2-one (17 mg, 0.031 mmole) in ethanol (1 mL) is added a 40% solution of dimethylamine (11 mg, 0.094 mmole). This mixture is heated at 80° C. in a sealed tube 16 h. The reaction is concentrated and lyophilized to provide 4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-1-[1-(2-dimethylamino-pyrimidin-4-yl)-piperidin-4-ylmethyl]-piperazin-2-one. 1H NMR (300 MHz, CDCl3) d 7.93-7.84 (m, 4H), 7.48 (dd, 1H), 5.84 (d, 1H), 4.32 (d, 2H), 3.87 (s, 2H), 3.47 (s, 4H), 3.26 (d, 2H), 3.14 (s, 6H), 1.99-1.90 (m, 1H), 1.62 (d, 2H), 1.27-1.17 (m, 2H); MS (Ion spray) 549 (M+H)+.

Workup

concentrationThe reaction is concentrated

Sources & evidence

ORD record: ord-adefd0dfaa224c9b98e6a41d1ea0cf35
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612075B2

Reaction notes

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