Bms-973013 → 4-(3,4-Dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-2-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-benzonitrile

HRID 469409Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.[CH3:17][N:18]1[C:22]2[C:23]([CH3:38])=[CH:24][C:25]([C:27]([C:29]3[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[C:31](F)[CH:30]=3)=[O:28])=[CH:26][C:21]=2[O:20][C:19]1=[O:39]>CN(C=O)C>[CH3:17][N:18]1[C:22]2[C:23]([CH3:38])=[CH:24][C:25]([C:27]([C:29]3[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[C:31]([N:1]4[CH2:2][CH2:3][CH:4]([N:7]5[C:15]6[C:10](=[N:11][CH:12]=[CH:13][CH:14]=6)[NH:9][C:8]5=[O:16])[CH2:5][CH2:6]4)[CH:30]=3)=[O:28])=[CH:26][C:21]=2[O:20][C:19]1=[O:39]

Participants

Conditions

Temperature: 300 °C

Procedure

0.26 g (1.2 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one and 93 mg (0.30 mmol) 4-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-2-fluoro-benzonitrile were combined and heated to 300° C. for approx. 10 min. Then the mixture was dissolved in DMF and purified by preparative HPLC-MS. The fractions containing the product were combined and the organic solvent was evaporated down. The residue was neutralised with 1N aqueous sodium hydroxide solution, the precipitate formed was suction filtered, washed with water and dried.

Workup

custompurified by preparative HPLC-MS
additionThe fractions containing the product
customthe organic solvent was evaporated down
customthe precipitate formed
filtrationfiltered
washwashed with water
customdried

Sources & evidence

ORD record: ord-20de981dacc4436c8c382f6dde0e97b0
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629137B2

Reaction notes

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