Methyl chloroformate → HCID 178501950, compound

HRID 2388990Notes

Reaction equation

HRID 2388990 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])=[N:25][NH:24][C:21]3=[N:22][CH:23]=2)=[CH:14][C:8]=1[C:9]([N:11]([CH3:13])[CH3:12])=[O:10]>ClCCl>[CH3:5][O:4][C:2](=[O:3])[NH:6][C:7]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])=[N:25][NH:24][C:21]3=[N:22][CH:23]=2)=[CH:14][C:8]=1[C:9](=[O:10])[N:11]([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 178489397HCID 178489397, compound

Product 1

HCID 178501950HCID 178501950, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl chloroformate (42 ul, 0.53 mmol) was added dropwise to a solution of 2-amino-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4,b]pyridin-5-yl]-N,N-dimethyl-benzamide (21 mg, 0.05 mmol) in dichloromethane/saturated aqueous sodium bicarbonate (1:1) at 0° C. The mixture was stirred for another 3 hours, allowing to slowly warm to room temperature. The reaction was washed three times with water (5 ml), dried over sodium sulfate and concentrated to dryness. The crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexane to afford {2-dimethylcarbamoyl-4[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-carbamic acid methyl ester (4.9 mg, 21% yield). 1H NMR (500 MHz, DMSO-d6) δ 2.88 (d, 6H), 3.58 (s, 3H), 3.77 (s, 3H), 7.03 (m, 1H), 7.15 (d, 1H), 7.40 (m, 1H), 7.58 (s, 1H), 7.64 (d, 1H), 7.73 (d, 1H), 8.27 (s, 1H), 8.78 (s, 1H), 9.03 (s, 1H). 13.75 (s, 1H); MS: m/z 446.1 (M+H+).

Workup

  1. washThe reaction was washed three times with water (5 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexane

Sources & evidence

ORD record
ord-209b96ac35bb48f5a08a3a54c4980350
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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