Tert-butyl 3-amino-3-phenylpropylcarbamate → HCID 178453506, compound

HRID 1809745Notes

Reaction equation

HRID 1809745 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[C:19]3[NH:21][N:22]=[C:23]([C:24]4[CH:29]=[CH:28][N:27]=[C:26](S(C)=O)[N:25]=4)[C:18]3=[CH:17][N:16]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:34]([O:38][C:39](=[O:51])[NH:40][CH2:41][CH2:42][CH:43]([NH2:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([CH3:37])([CH3:36])[CH3:35]>>[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[C:19]3[NH:21][N:22]=[C:23]([C:24]4[CH:29]=[CH:28][N:27]=[C:26]([NH:50][CH:43]([C:44]5[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=5)[CH2:42][CH2:41][NH:40][C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:51])[N:25]=4)[C:18]3=[CH:17][N:16]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 57826906Tert-butyl 3-amino-3-phenylpropylcarbamateHCID 178504618HCID 178504618, compound

Product 1

HCID 178453506HCID 178453506, compoundYield 7.1%

Conditions

Temperature
140 °C

Procedure

The mixture of {4-[3-(2-methanesulfinyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (from Example 9 supra) (300 mg, 0.64 mmol) and (3-amino-3-phenyl-propyl)-carbamic acid tert-butyl ester (from Example 2 supra) (635 mg, 2.6 mmol) was heated at 140° C. with stirring for 2 hours. The resulting oil was purified by chromatography (silica gel, dichloromethane:methanol, 50:1) and then further purified by prep-HPLC to afford (4-{3-[2-(3-tert-butoxycarbonylamino-1-phenyl-propylamino)-pyrimidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino}-cyclohexyl)-carbamic acid tert-butyl ester (30 mg, 7.1%).

Workup

  1. customThe resulting oil was purified by chromatography (silica gel, dichloromethane:methanol, 50:1)
  2. customfurther purified by prep-HPLC

Sources & evidence

ORD record
ord-68fc2c93557741c08abf604c1940b5ba
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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