Hydrochloric Acid → HCID 67429972, compound

HRID 1661088Notes

Reaction equation

[CH2:1]([C@H:8]([NH:24][C:25]([C:27]1[CH:28]=[C:29]([Cl:45])[CH:30]=[C:31]2[C:36]=1[N:35]=[CH:34][N:33]([CH:37]([CH2:41][CH2:42][CH3:43])[CH2:38][CH2:39][CH3:40])[C:32]2=[O:44])=[O:26])[C@H:9]([OH:23])[CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(OCC)C.O1CCOCC1>[ClH:45].[CH2:1]([C@H:8]([NH:24][C:25]([C:27]1[CH:28]=[C:29]([Cl:45])[CH:30]=[C:31]2[C:36]=1[N:35]=[CH:34][N:33]([CH:37]([CH2:41][CH2:42][CH3:43])[CH2:38][CH2:39][CH3:40])[C:32]2=[O:44])=[O:26])[C@H:9]([OH:23])[CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:20])[F:22])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 5 °C

Procedure

100 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]-amino}propyl]-6-chloro-4-oxo-3-(1-propylbutyl)-3,4-dihydroquinazoline-8-carboxamide are dissolved in 1.2 cm3 of ethyl ether at a temperature close to 20° C. 0.3 cm3 of a 4M solution of hydrochloric acid in dioxane is added, while stirring and under argon, at a temperature of 5° C. The reaction mixture precipitates, then the precipitate is dissolved. 5 cm3 of ethyl ether are added. The solution is concentrated under reduced pressure (5 kPa). 95 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-6-chloro-4-oxo-3-(1-propylbutyl)-3,4-dihydroquinazoline-8-carboxamide hydrochloride (1:1) are obtained in the form of an amorphous beige.

Workup

customclose to 20° C
customThe reaction mixture precipitates
dissolutionthe precipitate is dissolved
addition5 cm3 of ethyl ether are added
concentrationThe solution is concentrated under reduced pressure (5 kPa)

Sources & evidence

ORD record: ord-9d286766e46b4cefbdeadb47ed0f24dd
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030320B2

Reaction notes

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