(S)-tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamate → (S)-tert-butyl 1-(5-(6-bromo-3-propionylquinolin-4-ylamino)pyridin-2-yl)piperidin-3-ylcarbamate

HRID 2271608Notes

Reaction equation

HRID 2271608 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:15])[CH2:13][CH3:14])=[C:5]2Cl.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:25]2)=[N:22][CH:23]=1>>[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:15])[CH2:13][CH3:14])=[C:5]2[NH:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])[CH2:25]2)=[N:22][CH:23]=1

Participants

3

Reactant 2

HCID 66715841(S)-tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamateHCID 866928451-(6-Bromo-4-chloroquinolin-3-yl)propan-1-one

Product 1

HCID 86692876(S)-tert-butyl 1-(5-(6-bromo-3-propionylquinolin-4-ylamino)pyridin-2-yl)piperidin-3-ylcarbamateYield 30%

Procedure

Following general procedure C, 1-(6-bromo-4-chloroquinolin-3-yl)propan-1-one (301 mg, 1.02 mmol) was reacted with (S)-tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamate (600 mg, 2.05 mmol) to obtain the desired product (168 mg, 30%) as an purple semi-solid.: ESI MS m/z 554 [C27H32BrN5O3+H]+.

Sources & evidence

ORD record
ord-eae673bb348c4de8a47be4051ba79330
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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