2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide → HCID 86686638, compound
Reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[N:14]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]2[N:9]=[C:10](Cl)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[C:21]([O:25][C:26]([N:28]1[CH:33]2[CH2:34][CH2:35][CH2:36][CH:29]1[CH2:30][N:31]([C:37]([C:39]1[CH:40]=[N:41][C:42]([NH2:45])=[CH:43][CH:44]=1)=[O:38])[CH2:32]2)=[O:27])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26]([N:28]1[CH:29]2[CH2:36][CH2:35][CH2:34][CH:33]1[CH2:32][N:31]([C:37]([C:39]1[CH:40]=[N:41][C:42]([NH:45][C:10]3[N:11]=[CH:12][C:7]4[CH:6]=[C:5]([C:3](=[O:4])[N:2]([CH3:20])[CH3:1])[N:14]([CH:15]5[CH2:19][CH2:18][CH2:17][CH2:16]5)[C:8]=4[N:9]=3)=[CH:43][CH:44]=1)=[O:38])[CH2:30]2)=[O:27])([CH3:24])([CH3:22])[CH3:23]Participants
Procedure
Following general N—C coupling procedure 1, 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (100 mg, 0.342 mmol, 1.0 eq) was combined with 3-(6-Amino-pyridine-3-carbonyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester (130 mg, 0.376 mmol, 1.1 eq) which gave 3-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridine-3-carbonyl]-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester (121 mg) in 59% yield. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.51 (s, 10H) 1.56-1.70 (m, 3H) 1.70-1.81 (m, 3H) 1.88 (br. s., 3H) 2.05-2.24 (m, 6H) 2.50-2.67 (m, 2H) 3.18 (s, 7H) 3.55 (br. s., 1H) 3.91 (br. s., 1H) 4.25 (br. s., 1H) 4.78-4.90 (m, 1H) 6.50 (s, 1H) 7.80 (dd, J=8.84, 2.27 Hz, 1H) 8.28 (br. s., 1H) 8.41 (s, 1H) 8.59 (d, J=8.59 Hz, 1H) 8.78 (s, 1H); MS/m/z 603.6 (M+H)+.
Sources & evidence
- ORD record
- ord-d9c84675423e40ea99a502c440cee376
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957074B2
Reaction notes
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