Hydrochloric Acid → HCID 67431762, compound

HRID 1661090Notes

Reaction equation

HRID 1661090 reaction equation
[CH2:1]([C@H:8]([NH:24][C:25]([C:27]1[CH:28]=[CH:29][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.[ClH:45]>C(OCC)C.O1CCOCC1>[ClH:45].[CH2:1]([C@H:8]([NH:24][C:25]([C:27]1[CH:28]=[CH:29][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:22])[F:20])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 25204456HCID 25204456, compound

Product 1

HCID 67431762HCID 67431762, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
5 °C

Procedure

180 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]-amino}propyl]-4-oxo-3-(1-propylbutyl)-3,4-dihydroquinazoline-8-carboxamide are dissolved in 2.5 cm3 of ethyl ether at a temperature close to 20° C. 0.53 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. The suspension is stirred for 10 min then the stirring is stopped in order to remove the supernatant. 5 cm3 of ethyl ether are again added. This operation is carried out 3 times. The last suspension is then concentrated under reduced pressure (5 kPa). 160 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-4-oxo-3-(1-propylbutyl)-3,4-dihydroquinazoline-8-carboxamide hydrochloride (1:1) are obtained in the form of a pale yellow solid.

Workup

  1. customclose to 20° C
  2. customThe reaction mixture precipitates
  3. stirringThe suspension is stirred for 10 min
  4. customto remove the supernatant
  5. addition5 cm3 of ethyl ether are again added
  6. concentrationThe last suspension is then concentrated under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-4c1cabff8e204faf98156ac08fe7152a
Source dataset
uspto-grants-2011_10
Patent number
US08030320B2

Reaction notes

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