2-Cyanopyrimidine-5-boronic acid pinacol ester → HCID 178454019, compound

HRID 2271689Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]1.CC1(C)C(C)(C)OB([C:40]2[CH:41]=[N:42][C:43]([C:46]#[N:47])=[N:44][CH:45]=2)O1>>[C:46]([C:43]1[N:44]=[CH:45][C:40]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[C:5]3[NH:17][C@H:18]2[CH2:19][CH2:20][C@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:28])[CH3:29])[CH2:22][CH2:23]2)=[CH:41][N:42]=1)#[N:47]

Participants

Reactant 2

HCID 164142762-Cyanopyrimidine-5-boronic acid pinacol ester

HCID 178454009HCID 178454009, compound

Product 1

HCID 178454019HCID 178454019, compoundYield 101.4%

Procedure

Following general procedure D, tert-butyl trans-4-[6-bromo-3-(cyclopropanecarbonyl)quinolin-4-ylamino]cyclohexylcarbamate (49 mg, 0.100 mmol) was reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2-carbonitrile (46 mg, 0.200 mmol) to afford the crude product (52 mg): ESI MS m/z 513 [C29H32N6O3+H]+.

Sources & evidence

ORD record: ord-e9724492318147ed9bc91068fedb6c41
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

Loading…