Triethylamine → HCID 72699960, compound

HRID 715830Notes

Reaction equation

HRID 715830 reaction equation
[N:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:10]1[CH:11]=[CH:12][N:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:20][C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([CH:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)=[CH:24][CH:23]=3)=[CH:15][C:14]=12.C(N(CC)CC)C>CN1CCCC1=O>[N:10]1[CH:11]=[CH:12][N:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:20][C:21](=[O:34])[C:22]3[CH:23]=[CH:24][C:25]([CH:28]4[CH2:33][CH2:32][N:31]([C:7]([N:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)=[O:8])[CH2:30][CH2:29]4)=[CH:26][CH:27]=3)=[CH:15][C:14]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2420851-Piperidinecarbonyl chlorideHCID 86701980HCID 86701980, compound

Product 1

HCID 72699960HCID 72699960, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of piperidine-1-carbonyl chloride (0.033 g, 0.224 mmol) in N-methyl-2-pyrrolidinone (1 mL) was treated with N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)-benzamide (0.05 g, 0.150 mmol) and triethylamine (0.042 ml, 0.299 mmol) and the reaction mixture was stirred at room temperature for 18 hours. The mixture was purified by reverse-phase HPLC to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.24 (t, J=5.9 Hz, 1H), 8.84 (d, J=7.0 Hz, 1H), 8.30 (d, J=2.1 Hz, 1H), 8.13 (d, J=2.1 Hz, 1H), 7.91-7.84 (m, 2H), 7.76 (s, 1H), 7.50-7.44 (m, 1H), 7.42-7.36 (m, 2H), 4.67 (d, J=5.8 Hz, 2H), 3.71-3.62 (m, 2H), 3.16-3.10 (m, 4H), 2.89-2.68 (m, 3H), 1.81-1.72 (m, 2H), 1.68-1.44 (m, 8H); MS (ESI(+)) m/e 446 (M+H)+.

Workup

  1. customThe mixture was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-3468856c4ad94421a44a125bd6d50f4a
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

Loading…