Chlorosuccinimide → HCID 86701953, compound

HRID 717939Notes

Reaction equation

HRID 717939 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([NH:10][C:11](=[O:29])[NH:12][C:13]3[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)=[O:18])=[CH:15][CH:14]=3)[CH:7]=[CH:6][C:5]=12.[Cl:30]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:30][C:3]1[N:4]2[CH:9]=[C:8]([NH:10][C:11]([NH:12][C:13]3[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)=[O:18])=[CH:15][CH:14]=3)=[O:29])[CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 72700550HCID 72700550, compound

Product 1

HCID 86701953HCID 86701953, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-(3-imidazo[1,2-a]pyridin-6-ylureido)-N-((tetrahydro-2H-pyran-2-yl)methyl)benzamide (0.016 g, 0.041 mmol) in chloroform (0.813 ml) was treated with N-chlorosuccinimide (5.70 mg, 0.043 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under a stream of nitrogen and purified using normal phase chromatography to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.11 (s, 1H), 9.02 (s, 1H), 8.89-8.85 (m, 1H), 8.35 (t, J=5.8 Hz, 1H), 7.85-7.79 (m, 2H), 7.69-7.60 (m, 2H), 7.58-7.52 (m, 2H), 7.19 (dd, J=9.5, 2.0 Hz, 1H), 3.91-3.83 (m, 1H), 3.46-3.19 (m, 4H), 1.80-1.73 (m, 1H), 1.66-1.57 (m, 1H), 1.49-1.36 (m, 3H), 1.26-1.09 (m, 1H); MS (ESI(+)) m/e 428 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under a stream of nitrogen
  2. custompurified

Sources & evidence

ORD record
ord-f118060fd7ee4521a16a426fefbf6ba3
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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