N-(tert-butoxycarbonyl)glycine → (2-{4-[6-(7-cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester
Reaction equation
Cl.[CH3:2][N:3]([CH3:33])[C:4]([C:6]1[N:27]([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:9]2[N:10]=[C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[CH:17][N:16]=3)[N:12]=[CH:13][C:8]=2[CH:7]=1)=[O:5].[C:34]([NH:41][CH2:42][C:43](O)=[O:44])([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>>[C:37]([O:36][C:34](=[O:35])[NH:41][CH2:42][C:43]([N:24]1[CH2:23][CH2:22][N:21]([C:18]2[CH:17]=[N:16][C:15]([NH:14][C:11]3[N:12]=[CH:13][C:8]4[CH:7]=[C:6]([C:4](=[O:5])[N:3]([CH3:33])[CH3:2])[N:27]([CH:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)[C:9]=4[N:10]=3)=[CH:20][CH:19]=2)[CH2:26][CH2:25]1)=[O:44])([CH3:40])([CH3:38])[CH3:39]Participants
3
Procedure
By repeating procedures described in Example 88, 7-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide hydrochloride (150 mg, 0.318 mmol), N—BOC-glycine (56 mg, 0.318 mmol) gave a crude product which is purified by SiO2 chromatography, eluting with 0-7% methanol/dichloromethane to give (2-{4-[6-(7-cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester which is used directly in the next step.
Workup
- customgave a crude product which
- customis purified by SiO2 chromatography
- washeluting with 0-7% methanol/dichloromethane
Sources & evidence
- ORD record
- ord-56cd6e8688c045ff925a447d59c8c371
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685980B2
Reaction notes
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