Hydrogen Bromide → HCID 68764925, compound

HRID 1455409Notes

Reaction equation

Br.[NH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C@H:8]2[CH2:13][CH2:12][C@@H:11]([N:14]([CH:16]([CH3:18])[CH3:17])[CH3:15])[CH2:10][C@H:9]2[CH2:19][CH3:20])[C:4]1=[O:21].C(N(CC)CC)C.Cl[C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[C:37]([C:40]([F:43])([F:42])[F:41])[CH:38]=2)[N:33]=[CH:32][N:31]=1>CCO>[CH2:19]([C@@H:9]1[CH2:10][C@H:11]([N:14]([CH:16]([CH3:17])[CH3:18])[CH3:15])[CH2:12][CH2:13][C@@H:8]1[N:5]1[CH2:6][CH2:7][C@H:3]([NH:2][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([C:40]([F:42])([F:43])[F:41])[CH:38]=3)[N:33]=[CH:32][N:31]=2)[C:4]1=[O:21])[CH3:20]

Participants

Conditions

Temperature: 80 °C

Procedure

A sample of the bis-HBr salt of (S)-3-amino-1-((1S,2R,4R)-2-ethyl-4-(isopropyl(methyl)amino)cyclohexyl)pyrrolidin-2-one (147 mg) was dissolved in EtOH (5 mL) and the resulting solution was charged with triethylamine (0.55 mL) and 4-chloro-6-trifluoromethylquinazoline (183 mg) before being heated at 80° C. for 14 h. The reaction was cooled and concentrated under reduced pressure, and the residue was partitioned between diethyl ether and water. The organic phase was extracted twice with water. The combined aqueous extracts were lyophilized and the resultant powder was purified by RP-HPLC to afford (S)-1-((1S,2R,4R)-2-ethyl-4-(isopropyl(methyl)amino)cyclohexyl)-3-(6-(trifluoromethyl)quinazolin-4-ylamino)pyrrolidin-2-one. MS found: (M+H)+=478.4.

Workup

temperatureThe reaction was cooled
concentrationconcentrated under reduced pressure
customthe residue was partitioned between diethyl ether and water
extractionThe organic phase was extracted twice with water
customthe resultant powder was purified by RP-HPLC

Sources & evidence

ORD record: ord-a5a012ace8224ac4afb8ae8ff9269325
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482335B2

Reaction notes

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