Chlorosuccinimide → HCID 86701971, compound

HRID 717952Notes

Reaction equation

HRID 717952 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=[O:30])[C:13]3[CH:18]=[CH:17][C:16]([CH:19]4[CH2:24][CH2:23][N:22]([C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH2:21][CH2:20]4)=[CH:15][CH:14]=3)=[CH:6][C:5]=12.[Cl:31]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:31][C:3]1[N:4]2[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=[O:30])[C:13]3[CH:14]=[CH:15][C:16]([CH:19]4[CH2:24][CH2:23][N:22]([C:25](=[O:29])[CH:26]([CH3:27])[CH3:28])[CH2:21][CH2:20]4)=[CH:17][CH:18]=3)=[CH:6][C:5]2=[N:1][CH:2]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86701972HCID 86701972, compound

Product 1

HCID 86701971HCID 86701971, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-isobutyrylpiperidin-4-yl)benzamide (0.025 g, 0.062 mmol) in chloroform (1.030 ml) was treated with N-chlorosuccinimide (9.49 mg, 0.071 mmol) and the reaction was stirred at ambient temperature for 16 hours. The reaction was concentrated under a stream of warm nitrogen. The residue was purified by normal phase chromatography to give the title compound. 1H NMR (500 MHz, methanol-d4) δ ppm 8.67 (d, J=7.0 Hz, 1H), 8.11 (s, 1H), 7.89-7.83 (m, 2H), 7.81 (s, 1H), 7.57 (dd, J=7.1, 1.5 Hz, 1H), 7.43-7.37 (m, 2H), 4.80-4.75 (m, 2H), 4.75-4.67 (m, 1H), 4.25-4.16 (m, 1H), 3.28-3.18 (m, 1H), 3.07-2.88 (m, 2H), 2.79-2.66 (m, 1H), 2.02-1.85 (m, 2H), 1.75-1.53 (m, 2H), 1.17-1.08 (m, 6H); MS (ESI(+)) m/e 439 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated under a stream of warm nitrogen
  2. customThe residue was purified by normal phase chromatography

Sources & evidence

ORD record
ord-22e11f51522d4af78db2c1c737164111
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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