Bromoacetyl chloride → HCID 178428327, compound

HRID 2046972Notes

Reaction equation

HRID 2046972 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:8]([CH3:17])=[CH:7][C:6]=1[NH:18][C:19]1[N:24]=[C:23]2[NH:25][N:26]=[C:27]([CH3:28])[C:22]2=[C:21]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])[N:20]=1)([CH3:3])[CH3:2].[Br:42][CH2:43][C:44](Cl)=[O:45]>C(Cl)Cl>[Br:42][CH2:43][C:44]([N:14]1[CH2:15][CH2:16][CH:11]([C:9]2[CH:10]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[C:6]([NH:18][C:19]3[N:24]=[C:23]4[NH:25][N:26]=[C:27]([CH3:28])[C:22]4=[C:21]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])[N:20]=3)=[CH:7][C:8]=2[CH3:17])[CH2:12][CH2:13]1)=[O:45]

Participants

4

Reactant 2

HCID 89602Bromoacetyl chlorideHCID 178428323HCID 178428323, compound

Product 1

HCID 178428327HCID 178428327, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N6-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine (50 mg, 0.087 mmol) in CH2Cl2 (3 mL) was added bromoacetyl chloride (10 uL, 0.095 mmol) dropwise at 0° C. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography, eluting with a gradient of EtOAc/hexane (0-100%) to give the title compound (2-bromo-1-(4-(5-isopropoxy-4-(4-(2-(isopropylsulfonyl)phenylamino)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methylphenyl)piperidin-1-yl)ethanone) as a light yellow solid. MS: m/z=698.2 (M+1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with a gradient of EtOAc/hexane (0-100%)

Sources & evidence

ORD record
ord-ca939a9b8de1493ba53e07933b3bb829
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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