3-Benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane → HCID 67355729, 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]([OH:22])=O)=[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.[CH2:30]([N:37]1[CH2:44][CH:43]2[O:45][CH:39]([CH2:40][NH:41][CH2:42]2)[CH2:38]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH3:27][N:26]([CH3:28])[C:25]([C:7]1[N:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:10]2[N:11]=[C:12]([NH:15][C:16]3[CH:24]=[CH:23][C:19]([C:20]([N:41]4[CH2:40][CH:39]5[O:45][CH:43]([CH2:44][N:37]([CH2:30][C:31]6[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=6)[CH2:38]5)[CH2:42]4)=[O:22])=[CH:18][N:17]=3)[N:13]=[CH:14][C:9]=2[CH:8]=1)=[O:29]Participants
Procedure
Following general amide formation method 1, 6-(7-cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-nicotinic acid (200 mg, 0.507 mmol, 1.0 eq) was combined with 3-benzyl-9-oxa-3,7-diaza-bicyclo[3.3.1]nonane (162 mg, 0.558 mmol, 1.1 eq) (Reference: PCT Int. Appl. 2006137769, 2 Dec. 2006) which gave 2-[5-(7-Benzyl-9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carbonyl)-pyridin-2-ylamino]-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide as solid (131 mg) in 39% yield. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.64-1.83 (m, 3H) 2.04 (d, J=7.07 Hz, 2H) 2.12 (d, J=6.57 Hz, 2H) 2.58 (br. s., 4H) 3.18 (s, 6H) 3.45 (br. s., 3H) 3.49-3.57 (m, 1H) 3.67-3.80 (m, 1H) 3.84 (br. s., 2H) 4.02 (br. s., 1H) 4.66-4.88 (m, 2H) 6.51 (s, 1H) 7.22-7.28 (m, 1H) 7.31-7.37 (m, 5H) 7.85 (dd, J=8.84, 2.27 Hz, 1H) 8.27 (br. s., 1H) 8.43 (s, 1H) 8.51 (br. s., 1H) 8.78 (s, 1H). MS m/z 595.6 (M+H)+.
Sources & evidence
- ORD record
- ord-55ef473ab1294c31b97a033705393aac
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309252B2
Reaction notes
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