tert-butyl rac-(3R,4R)-4-(6-bromo-4-oxobenzo[h]quinazolin-3(4H)-yl)-3-hydroxypiperidine-1-carboxylate → HCID 86666963, compound

HRID 1774929Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=13)[N:8]=[CH:7][N:6]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH:17]1[OH:29])[C:5]2=[O:30].[Cl-].[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][Zn+])=[CH:35][N:34]=1>ClCCl>[Cl:32][C:33]1[N:34]=[CH:35][C:36]([CH2:39][C:2]2[CH:3]=[C:4]3[C:9](=[C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=24)[N:8]=[CH:7][N:6]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:18][CH:17]2[OH:29])[C:5]3=[O:30])=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a dry 25 mL round bottom flask containing tert-butyl rac-(3R,4R)-4-(6-bromo-4-oxobenzo[h]quinazolin-3(4H)-yl)-3-hydroxypiperidine-1-carboxylate (0.163 g, 0.344 mmol) under N2(g) was added (2-chloro-5-pyridyl)methylzinc chloride (0.5 M in THF, 2.06 mL, 1.03 mmol) and tetrakis (triphenylphosphine)palladium (0) (10 mol %). The reaction was heated to reflux at 90° C. for 20 h, cooled to room temperature, and diluted with dichloromethane. Hexanes were added to the solution and the resultant beige precipitate was collected via filtration, washed with dichloromethane and hexanes, and dried on high vac to provide crude tert-butyl rac-(3R,4R)-4-[6-[(6-chloropyridin-3-yl)methyl]-4-oxobenzo[h]quinazolin-3(4H)-yl]-3-hydroxypiperidine-1-carboxylate that gave a mass ion (ES+) of 520.9 for M+H+.

Workup

temperatureThe reaction was heated
temperaturecooled to room temperature
filtrationthe resultant beige precipitate was collected via filtration
washwashed with dichloromethane and hexanes
customdried on high vac

Sources & evidence

ORD record: ord-e76d9cf7a627410db55e741c1f70e81d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260418B2

Reaction notes

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