8-Oxa-3-azabicyclo[3.2.1]octane → HCID 67354909, 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.[CH:30]12[O:37][CH:34]([CH2:35][CH2:36]1)[CH2:33][NH:32][CH2:31]2>>[CH3:28][N:26]([CH3:27])[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:32]4[CH2:31][CH:30]5[O:37][CH:34]([CH2:35][CH2:36]5)[CH2:33]4)=[O:21])=[CH:18][N:17]=3)[N:13]=[CH:14][C:9]=2[CH:8]=1)=[O:29]Participants
3
Procedure
Following general amide formation method 3, 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid (528 mg, 1.34 mmole) was combined with 8-Oxa-3-aza-bicyclo[3.2.1]octane (199 mg, 1.34 mmol) which gave 7-Cyclopentyl-2-[5-(8-oxa-3-aza-bicyclo[3.2.1]octane-3-carbonyl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (213 mg, 0.435 mmol) in 32.5% yield. 1H NMR (400 MHz, CDCl3) δ ppm 1.74 (m, 8H), 2.07 (m, 5H), 2.58 (m, 2H), 3.17 (s, 7H), 4.81 (dd, 1H), 6.48 (s, 1H), 7.79 (dd, 8.30 (s, 1H), 8.39 (d, 1H), 8.56 (d, 1H), 8.77 (s, 1H) MS m/z 490.5 (M+H)+.
Sources & evidence
- ORD record
- ord-35d0080f533f401ebb2106a5fb6a8f2b
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309252B2
Reaction notes
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