7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide → 7-Cyclopentyl-2-[5-(4-oxo-8-oxa-3,10-diaza-bicyclo[4.3.1]dec-3-yl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide
Reaction equation
C(OC([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:26]3[N:27]=[CH:28][C:29]4[CH:34]=[C:33]([C:35](=[O:39])[N:36]([CH3:38])[CH3:37])[N:32]([CH:40]5[CH2:44][CH2:43][CH2:42][CH2:41]5)[C:30]=4[N:31]=3)=[CH:23][CH:24]=1)[C:12](=[O:18])[CH2:13]2)=O)(C)(C)C.CN(C)C(C1NC2N=CN=CC=2C=1)=O>>[CH3:37][N:36]([CH3:38])[C:35]([C:33]1[N:32]([CH:40]2[CH2:44][CH2:43][CH2:42][CH2:41]2)[C:30]2[N:31]=[C:26]([NH:25][C:22]3[CH:23]=[CH:24][C:19]([N:11]4[C:12](=[O:18])[CH2:13][CH:14]5[NH:8][CH:9]([CH2:17][O:16][CH2:15]5)[CH2:10]4)=[CH:20][N:21]=3)[N:27]=[CH:28][C:29]=2[CH:34]=1)=[O:39]Participants
Reactant 2
Product 1
Procedure
Following deprotection method 1, 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 (470 mg, 0.777 mmol) was converted to 7-Cyclopentyl-2-[5-(4-oxo-8-oxa-3,10-diaza-bicyclo[4.3.1]dec-3-0)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (231 mg, 0.457 mmol) in 58.8% yield. 1H NMR (400 MHz, D6 DMSO) δ 10.2 (s, 1H, broad), 9.05 (s, 1H, broad), 8.35 (s, 1H), 8.0 (d, 1H), 7.7 (d, 1H), 6.9 (s, 1H), 4.82 (m, 1H, broad), 4.6 (d, 1H), 4.25 (s, 1H, broad), 4.15 (s, 1H, broad), 3.82 (m, 1H, broad), 3.5 (d, 1H), 3.05 (s, 6H), 2.82 (m, 1H), 2.3 (m, 2H), 2.2-1.95 (m, 10H, broad), 1.89 (m, 1H), 1.65 (m, 2H) MS m/z 504.6 (M+H)
Sources & evidence
- ORD record
- ord-5d8efd07b28242309681aec0e5869cb8
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309252B2
Reaction notes
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