Chlorosuccinimide → HCID 57856246, compound

HRID 500746Notes

Reaction equation

HRID 500746 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)[C:6]([C:16]2[CH:17]=[C:18]3[CH:24]=[CH:23][NH:22][C:19]3=[N:20][CH:21]=2)=[N:5]1)([CH3:3])[CH3:2].[Cl:25]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:25][C:24]1[C:18]2[C:19](=[N:20][CH:21]=[C:16]([C:6]3[C:7]([C:9]4[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=4)=[CH:8][N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=3)[CH:17]=2)[NH:22][CH:23]=1

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 57856337HCID 57856337, compound

Product 1

HCID 57856246HCID 57856246, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture 4-(1-isopropyl-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-4-yl)pyridin-2-amine (H-1-10) (40 mg, 0.13 mmol) and N-chlorosuccinimide (19.3 mg, 0.14 mmol) in CH2Cl2 (2 ml) was stirred at room temperature for 18 hours. Another portion of N-chlorosuccinimide (5 mg, 0.04 mmol) was added and stirring continued at room temperature for an additional 4 hours. The reaction was concentrated under reduced pressure and the residue was purified by reverse phase HPLC to give 14 mg (31% yield) 4-(3-(3-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-isopropyl-1H-pyrazol-4-yl)pyridin-2-amine (H-1) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51 (d, J=6.82 Hz, 6H) 4.43-4.69 (m, 1H) 6.22-6.63 (m, 4H) 7.72 (d, J=2.78 Hz, 1H) 7.82 (d, J=5.81 Hz, 1H) 7.92 (d, J=1.77 Hz, 1H) 8.23 (s, 1H) 8.30 (d, J=2.02 Hz, 1H) 12.08 (d, J=1.77 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-dd72fdd3bcf146b28e08d2eb34a919d4
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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