7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide → 7-cyclopentyl-2-[5-((R,R)-2,5-diaza-bicyclo[2.2.1]heptane-2-carbonyl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide
Reaction equation
C(OC([N:8]1[CH2:13][C@H:12]2[CH2:14][C@@H:9]1[CH2:10][N:11]2[C:15]([C:17]1[CH:18]=[N:19][C:20]([NH:23][C:24]2[N:25]=[CH:26][C:27]3[CH:32]=[C:31]([C:33](=[O:37])[N:34]([CH3:36])[CH3:35])[N:30]([CH:38]4[CH2:42][CH2:41][CH2:40][CH2:39]4)[C:28]=3[N:29]=2)=[CH:21][CH:22]=1)=[O:16])=O)(C)(C)C.CN(C)C(C1NC2N=CN=CC=2C=1)=O>>[CH3:35][N:34]([CH3:36])[C:33]([C:31]1[N:30]([CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)[C:28]2[N:29]=[C:24]([NH:23][C:20]3[CH:21]=[CH:22][C:17]([C:15]([N:11]4[CH2:10][C@H:9]5[CH2:14][C@@H:12]4[CH2:13][NH:8]5)=[O:16])=[CH:18][N:19]=3)[N:25]=[CH:26][C:27]=2[CH:32]=1)=[O:37]Participants
3
Procedure
Following deprotection method 2, 5-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridine-3-carbonyl]-(R,R)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester was converted to 7-Cyclopentyl-2-[5-(R,R)-2,5-diaza-bicyclo[2.2.1]heptane-2-carbonyl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (20 mg) in 22% yield. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.65-1.85 (m, 4H) 2.03 (s, 2H) 2.06-2.19 (m, 6H) 2.59 (br. s., 2H) 3.18 (s, 7H) 3.33 (d, J=9.60 Hz, 1H) 3.52 (br. s., 1H) 3.78 (br. s., 2H) 4.72-4.94 (m, 1H) 6.38-6.54 (m, 1H) 7.96 (d, J=9.09 Hz, 1H) 8.56 (s, 1H) 8.61 (d, J=8.59 Hz, 1H) 8.84 (br. s., 1H); HRMS m/z, (M+H)+: 475.2582.
Sources & evidence
- ORD record
- ord-fa1d3222cd174668b911b90b75a143ff
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309252B2
Reaction notes
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