2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide → 3-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-4-oxo-8-oxa-3,10-diaza-bicyclo[4.3.1]decane-10-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:14]2[CH2:15][O:16][CH2:17][CH:9]1[CH2:10][N:11]([C:19]1[CH:20]=[N:21][C:22]([NH2:25])=[CH:23][CH:24]=1)[C:12](=[O:18])[CH2:13]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][N:27]([CH3:45])[C:28]([C:30]1[N:39]([CH:40]2[CH2:44][CH2:43][CH2:42][CH2:41]2)[C:33]2[N:34]=[C:35](Cl)[N:36]=[CH:37][C:32]=2[CH:31]=1)=[O:29]>>[C:1]([O:5][C:6]([N:8]1[CH:14]2[CH2:15][O:16][CH2:17][CH:9]1[CH2:10][N:11]([C:19]1[CH:20]=[N:21][C:22]([NH:25][C:35]3[N:36]=[CH:37][C:32]4[CH:31]=[C:30]([C:28](=[O:29])[N:27]([CH3:26])[CH3:45])[N:39]([CH:40]5[CH2:44][CH2:43][CH2:42][CH2:41]5)[C:33]=4[N:34]=3)=[CH:23][CH:24]=1)[C:12](=[O:18])[CH2:13]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
3
Reactant 2
Product 1
Procedure
Following general N—C coupling procedure 1, 3-(6-Amino-pyridin-3-yl)-4-oxo-8-oxa-3,10-diaza-bicyclo[4.3.1]decane-10-carboxylic acid tert-butyl ester (350 mg, 1.047 mmol) was combined with 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (337 mg, 1.151 mmol) which gave 3-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-4-oxo-8-oxa-3,10-diaza-bicyclo[4.3.1]decane-10-carboxylic acid tert-butyl ester (476 mg, 0.787 mmol) in 75% yield.
Sources & evidence
- ORD record
- ord-2a0aacf9283645e29e3b7e1f0b529ec5
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309252B2
Reaction notes
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