1-(6-Bromo-4-chloroquinolin-3-YL)ethanone → Tert-butyl 1-(5-(3-acetyl-6-bromoquinolin-4-ylamino)pyridin-2-yl)piperidin-3-ylcarbamate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2Cl.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH:25]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:24]2)=[N:21][CH:22]=1>>[C:12]([C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[NH:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]3[CH2:28][CH2:27][CH2:26][CH:25]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:24]3)=[N:21][CH:22]=1)=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)(=[O:14])[CH3:13]Participants
3
Procedure
Following general procedure B, 1-(6-bromo-4-chloroquinolin-3-yl)ethanone (194 mg, 0.681 mmol) was reacted with tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamate (210 mg, 0.821 mmol) to afford the desired product (205 mg, 55%) as a brown solid: ESI MS m/z 540, [C26H30BrN5O3+H]+
Sources & evidence
- ORD record
- ord-70d01c78feeb40288ad10a15f3389591
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120749B2
Reaction notes
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