Chlorosuccinimide → HCID 86701963, compound

HRID 717948Notes

Reaction equation

HRID 717948 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([NH:10][C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)=[CH:15][CH:14]=3)=[O:12])[CH:7]=[CH:6][C:5]=12.[Cl:32]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.CO>[Cl:32][C:3]1[N:4]2[CH:9]=[C:8]([NH:10][C:11]([C:13]3[CH:14]=[CH:15][C:16]([CH:19]4[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]4)=[CH:17][CH:18]=3)=[O:12])[CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 86701964HCID 86701964, compound

Product 1

HCID 86701963HCID 86701963, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of tert-butyl 4-(4-(imidazo[1,2-a]pyridin-6-ylcarbamoyl)phenyl)piperidine-1-carboxylate (0.015 g, 0.036 mmol) in chloroform (0.618 ml) and methanol (0.095 ml) was treated with N-chlorosuccinimide (5.24 mg, 0.039 mmol) and the reaction was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated under a stream of warm nitrogen. The residue was purified by normal phase flash chromatography to provide the title compound. 1H NMR (500 MHz, methanol-d4) δ ppm 9.23 (s, 1H), 7.93 (d, J=8.3 Hz, 2H), 7.62-7.51 (m, 3H), 7.42 (d, J=8.3 Hz, 2H), 4.27-4.19 (m, 2H), 2.96-2.76 (m, 3H), 1.90-1.82 (m, 2H), 1.70-1.57 (m, 2H), 1.48 (s, 9H); MS (ESI(+)) m/e 455 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-75cebed9391f4f47a3e9585ef5989233
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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