Benzenemethanamine, 3-chloro- → HCID 178452331, compound

HRID 1809786Notes

Reaction equation

HRID 1809786 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH:16][C:17]2[N:22]=[C:21]3[NH:23][N:24]=[C:25]([C:26]4[CH:31]=[CH:30][N:29]=[C:28](S(C)(=O)=O)[N:27]=4)[C:20]3=[CH:19][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH2:40][NH2:41]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH:16][C:17]2[N:22]=[C:21]3[NH:23][N:24]=[C:25]([C:26]4[CH:31]=[CH:30][N:29]=[C:28]([NH:41][CH2:40][C:39]5[CH:42]=[CH:43][CH:44]=[C:37]([Cl:36])[CH:38]=5)[N:27]=4)[C:20]3=[CH:19][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 77802Benzenemethanamine, 3-chloro-HCID 178452332HCID 178452332, compound

Product 1

HCID 178452331HCID 178452331, compound

Conditions

Temperature
130 °C

Procedure

The mixture of 4-{2-[3-(2-methanesulfonyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester (from Example 27 supra) (153 mg, 0.304 mmol) and 3-chlorobenzylamine (171 mg, 1.21 mmol) was heated at 130° C. with stirring for 3 hours. The resulting oil was purified by chromatography (silica gel, 7 g, 100-200 mesh, eluting with dichloromethane:methanol, 10:1) and further purified by prep-HPLC to afford 4-(2-{3-[2-(3-chloro-benzylamino)-pyrimidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino}-ethyl)-piperazine-1-carboxylic acid tert-butyl ester. (Yield 90 mg, 52%).

Workup

  1. customThe resulting oil was purified by chromatography (silica gel, 7 g, 100-200 mesh, eluting with dichloromethane:methanol, 10:1)
  2. customfurther purified by prep-HPLC

Sources & evidence

ORD record
ord-d71a16d1c58b45188c0a400dd679eab3
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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