6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid → HCID 67354854, compound
Reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[CH:8]=[C:7]2[C:25](=[O:29])[N:26]([CH3:28])[CH3:27])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C@H:30]12[CH2:37][C@H:33]([C@H:34]([OH:36])[CH2:35]1)[CH2:32][NH:31]2>>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:24]=[CH:23][C:19]([C:20]([N:31]5[CH2:32][C@@H:33]6[CH2:37][C@H:30]5[CH2:35][C@H:34]6[OH:36])=[O:21])=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[CH:8]=[C:7]2[C:25]([N:26]([CH3:28])[CH3:27])=[O:29])[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
Procedure
The 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid was combined with (1S,4S,5R)-2-azabicyclo[2.2.1]heptan-5-ol following amide formation method 3 which gave 7-cyclopentyl-2-(5-((1S,4S,5R)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carbonyl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (40 mg) in 60% yield. 1H NMR (400 MHz, CDCl3) δ ppm 9.51-9.43 (m, 0.3H, Rotamer) 9.43-9.35 (m, 0.7H, Rotamer) 8.87 (s, 1H) 8.66-8.60 (m, 0.3H, Rotamer) 8.60-8.52 (m, 0.7H, Rotamer+1H) 7.94-7.84 (m, 1H) 6.48 (s, 1H) 4.86-4.75 (m, 1H) 4.75-4.71 (m, 0.3H, Rotamer) 4.32-4.25 (m, 0.7H, Rotamer) 4.21-4.13 (m, 0.7H, Rotamer) 4.08-4.02 (m, 0.3H, Rotamer) 3.61-3.50 (m, 1H) 3.15 (s, 6H) 3.10-3.01 (m, 1H) 2.93-2.83 (m, 0.7H, Rotamer) 2.78-2.67 (m, 0.3H, Rotamer H) 2.65-2.50 (m, 3H) 2.36-2.20 (m, 1H) 2.15-1.99 (m, 4H) 1.99-1.88 (m, 1H) 1.80-1.65 (m, 2H) 1.59 (none, 2H). HR-MS (m/z MH+) 490.26 RT 4.34 min
Sources & evidence
- ORD record
- ord-23a4246986614a18ab9805ecb4ce3f62
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957074B2
Reaction notes
Loading…