tert-Butyl 3,9-diazabicyclo[4.2.1]nonane-9-carboxylate → HCID 67355434, 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:30]([O:34][C:35]([N:37]1[CH:43]2[CH2:44][CH2:45][CH:38]1[CH2:39][NH:40][CH2:41][CH2:42]2)=[O:36])([CH3:33])([CH3:32])[CH3:31]>>[C:30]([O:34][C:35]([N:37]1[CH:43]2[CH2:44][CH2:45][CH:38]1[CH2:39][N:40]([C:20]([C:19]1[CH:18]=[N:17][C:16]([NH:15][C:12]3[N:13]=[CH:14][C:9]4[CH:8]=[C:7]([C:25](=[O:29])[N:26]([CH3:28])[CH3:27])[N:6]([CH:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)[C:10]=4[N:11]=3)=[CH:24][CH:23]=1)=[O:21])[CH2:41][CH2:42]2)=[O:36])([CH3:33])([CH3:31])[CH3:32]Participants
3
Procedure
Following general amide formation method 3, 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid (0.2 g, 0.507 mmol) was combined with 3,9-diaza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester (0.136 g, 0.6 mmol) which gave 3-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridine-3-carbonyl]-3,9-diaza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester (0.269 g, 0.433 mmol) in 85% yield. MS m/z 602.7 (M+H)+.
Sources & evidence
- ORD record
- ord-42b45376219642f8a6620f89322f9cce
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957074B2
Reaction notes
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