Acetyl chloride → 1-(4-{3-[1-(1H-Benzoimidazole-2-carbonyl)-azetidin-3-YL]-pyrazin-2-YL}-3,6-dihydro-2H-pyridin-1-YL)-ethanone

HRID 1850332Notes

Reaction equation

Cl.[NH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]([N:13]1[CH2:16][CH:15]([C:17]2[C:22]([C:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=3)=[N:21][CH:20]=[CH:19][N:18]=2)[CH2:14]1)=[O:12].CCN(CC)CC.[C:36](Cl)(=[O:38])[CH3:37]>C(Cl)Cl>[NH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]([N:13]1[CH2:14][CH:15]([C:17]2[C:22]([C:23]3[CH2:24][CH2:25][N:26]([C:36](=[O:38])[CH3:37])[CH2:27][CH:28]=3)=[N:21][CH:20]=[CH:19][N:18]=2)[CH2:16]1)=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (1H-benzoimidazol-2-yl)-{3-[3-(1,2,3,6-tetrahydro-pyridin-4-yl)-pyrazin-2-yl]-azetidin-1-yl}-methanone hydrochloride (187 mg, 0.47 mmol) in dry CH2Cl2 (10 mL) was added Et3N (1 mL). The reaction mixture was cooled to 0° C. with an ice bath, and acetyl chloride (39 mg, 0.50 mmol) was added dropwise. After 1 h, the reaction mixture was warmed to RT, and stirred overnight. Then the reaction mixture was washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to give the crude product (170 mg, 0.42 mmol, 90% yield). ESI-MS (M+1): 403 calc. for C22H22N6O2 402.

Workup

temperaturethe reaction mixture was warmed to RT
washThen the reaction mixture was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-f58417ab48144247b7e8df16fd5fc798
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957073B2

Reaction notes

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