Triethylamine → HCID 178452584, compound

HRID 1037383Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[F:27][CH:28]([F:32])[C:29](O)=O.[C:33]([O:37][C:38](=[O:69])[NH:39][C:40]1([C:44]2[CH:49]=[CH:48][C:47]([C:50]3[C:59](=[O:60])[C:58]4[C:53](=[C:54]([NH2:62])[C:55]([NH2:61])=[CH:56][CH:57]=4)[O:52][C:51]=3[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)=[CH:46][CH:45]=2)[CH2:43][CH2:42][CH2:41]1)([CH3:36])([CH3:35])[CH3:34]>C(Cl)(Cl)(Cl)Cl.ClCCCl.C1CCCCC1.C(OCC)(=O)C>[C:33]([O:37][C:38](=[O:69])[NH:39][C:40]1([C:44]2[CH:45]=[CH:46][C:47]([C:50]3[C:59](=[O:60])[C:58]4[CH:57]=[CH:56][C:55]5[N:61]=[C:29]([CH:28]([F:32])[F:27])[NH:62][C:54]=5[C:53]=4[O:52][C:51]=3[C:63]3[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=3)=[CH:48][CH:49]=2)[CH2:43][CH2:42][CH2:41]1)([CH3:36])([CH3:34])[CH3:35]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of triphenylphosphine (126 mg, 0.48 mmol) in CCl4 (1 mL) at 0° C. was added triethylamine (67 μL, 0.48 mmol) and difluoroacetic acid (11 μL, 0.18 mmol). After 10 min, {1-[4-(7,8-diamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (80 mg, 0.16 mmol) in 1,2-dichloroethane (1 mL) was added, the temperature raised to 80° C. After 2.5 hours, the reaction mixture was allowed to cool to RT and the solution was directly subjected to flash chromatography (SiO2, 40% ethyl acetate in cyclohexane) to give the title compound as a pale yellow solid (64 mg, 72%). LCMS (Method G): RT=3.93 min, [M+H]+=558.

Workup

waitAfter 2.5 hours
temperatureto cool to RT

Sources & evidence

ORD record: ord-e4bd31b635ac4d2889f5200787b21705
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546376B2

Reaction notes

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