7-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one → 3-(3,4-Dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-5-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidin-1-yl]-benzonitrile

HRID 469400Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:20]=1.[CH3:21][N:22]1[C:26]2[C:27]([CH3:42])=[CH:28][C:29]([C:31]([C:33]3[CH:34]=[C:35]([CH:38]=[C:39](F)[CH:40]=3)[C:36]#[N:37])=[O:32])=[CH:30][C:25]=2[O:24][C:23]1=[O:43]>CN(C=O)C>[CH3:21][N:22]1[C:26]2[C:27]([CH3:42])=[CH:28][C:29]([C:31]([C:33]3[CH:34]=[C:35]([CH:38]=[C:39]([N:17]4[CH2:18][CH2:19][CH:14]([N:10]5[CH2:9][CH2:8][C:7]6[CH:20]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=6[NH:12][C:11]5=[O:13])[CH2:15][CH2:16]4)[CH:40]=3)[C:36]#[N:37])=[O:32])=[CH:30][C:25]=2[O:24][C:23]1=[O:43]

Participants

Conditions

Temperature: 300 °C

Procedure

0.22 g (0.80 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 0.12 g (0.40 mmol) 3-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-5-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 i. vac.

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 i

Sources & evidence

ORD record: ord-c005bb04c9914f5688a39ace33783ce0
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629137B2

Reaction notes

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