Benzenemethanamine, 3-chloro- → HCID 178451972, compound

HRID 1809781Notes

Reaction equation

HRID 1809781 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[N:21]=[C:20]3[NH:22][N:23]=[C:24]([C:25]4[CH:30]=[CH:29][N:28]=[C:27](S(C)=O)[N:26]=4)[C:19]3=[CH:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:34][C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH2:38][NH2:39]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[N:21]=[C:20]3[NH:22][N:23]=[C:24]([C:25]4[CH:30]=[CH:29][N:28]=[C:27]([NH:39][CH2:38][C:37]5[CH:40]=[CH:41][CH:42]=[C:35]([Cl:34])[CH:36]=5)[N:26]=4)[C:19]3=[CH:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 77802Benzenemethanamine, 3-chloro-HCID 178504620HCID 178504620, compound

Product 1

HCID 178451972HCID 178451972, compound

Conditions

Temperature
130 °C

Procedure

The mixture of 4-{[3-(2-methanesulfinyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (from Example 15 supra) (200 mg, 0.42 mmol) and 3-chlorobenzylamine (238 mg, 1.7 mmol) was heated at 130° C. with stirring for 2 hours. The resulting oil was purified by chromatography (silica gel, 7 g, 200-300 mesh, eluting with dichloromethane:methanol, 50:1 to 30:1) to afford 4-({3-[2-(3-chloro-benzylamino)-pyrimidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester. (Yield 200 mg, 86.2%).

Workup

  1. customThe resulting oil was purified by chromatography (silica gel, 7 g, 200-300 mesh, eluting with dichloromethane:methanol, 50:1 to 30:1)

Sources & evidence

ORD record
ord-3e91ea7a16244a1b8c15a797ef658197
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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