HCID 67355362, compound → HCID 86686642, compound
Reaction equation
[CH3:1][N:2]([CH3:24])[C:3]([C:5]1[N:14]([CH:15]2[CH2:20][CH2:19][N:18]([CH:21]3[CH2:23][CH2:22]3)[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:25]([O:29][C:30]([N:32]1[CH:37]2[CH2:38][CH2:39][CH:33]1[CH2:34][N:35]([C:40]([C:42]1[CH:43]=[N:44][C:45]([NH2:48])=[CH:46][CH:47]=1)=[O:41])[CH2:36]2)=[O:31])([CH3:28])([CH3:27])[CH3:26]>>[C:25]([O:29][C:30]([N:32]1[CH:33]2[CH2:39][CH2:38][CH:37]1[CH2:36][N:35]([C:40]([C:42]1[CH:43]=[N:44][C:45]([NH:48][C:10]3[N:11]=[CH:12][C:7]4[CH:6]=[C:5]([C:3](=[O:4])[N:2]([CH3:24])[CH3:1])[N:14]([CH:15]5[CH2:20][CH2:19][N:18]([CH:21]6[CH2:23][CH2:22]6)[CH2:17][CH2:16]5)[C:8]=4[N:9]=3)=[CH:46][CH:47]=1)=[O:41])[CH2:34]2)=[O:31])([CH3:28])([CH3:26])[CH3:27]Participants
Procedure
Using General Buchwald method 1, 2-Chloro-7-(1-cyclopropyl-piperidin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (95 mg, 0.273 mmol, 1.0 eq) was combined with 3-(6-Amino-pyridine-3-carbonyl)-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (100 mg, 0.300 mmol, 1.1 eq) to give 3-{6-[7-(1-Cyclopropyl-piperidin-4-yl)-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-pyridine-3-carbonyl}-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (131 mg, 71% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.46 (br. s., 2H) 0.54 (br. s., 2H) 1.52 (s, 10H) 1.61 (br. s., 2H) 1.71 (br. s., 2H) 1.88 (d, J=10.11 Hz, 3H) 1.96 (d, J=6.06 Hz, 2H) 2.37 (t, J=11.62 Hz, 2H) 2.79-3.01 (m, 2H) 3.20 (s, 10H) 3.63 (br. s., 2H) 4.27 (br. s., 2H) 4.41 (br. s., 2H) 6.50 (s, 1H) 7.69 (br. s., 1H) 8.22 (s, 1H) 8.41 (s, 1H) 8.63 (d, J=8.59 Hz, 1H) 8.77 (s, 1H); MS m/z 644.6 (M+H)+.
Sources & evidence
- ORD record
- ord-88ad14ef169f49e1b39590f0523a1ff3
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957074B2
Reaction notes
Loading…