Trifluoroacetic acid → HCID 178452583, compound

HRID 1037381Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C:27](O)([C:29]([F:32])([F:31])[F:30])=O.[C:34]([O:38][C:39](=[O:70])[NH:40][C:41]1([C:45]2[CH:50]=[CH:49][C:48]([C:51]3[C:60](=[O:61])[C:59]4[C:54](=[C:55]([NH2:63])[C:56]([NH2:62])=[CH:57][CH:58]=4)[O:53][C:52]=3[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)=[CH:47][CH:46]=2)[CH2:44][CH2:43][CH2:42]1)([CH3:37])([CH3:36])[CH3:35]>C(Cl)(Cl)(Cl)Cl.C1CCCCC1.C(OCC)(=O)C.ClCCCl>[C:34]([O:38][C:39](=[O:70])[NH:40][C:41]1([C:45]2[CH:46]=[CH:47][C:48]([C:51]3[C:60](=[O:61])[C:59]4[CH:58]=[CH:57][C:56]5[N:62]=[C:27]([C:29]([F:32])([F:31])[F:30])[NH:63][C:55]=5[C:54]=4[O:53][C:52]=3[C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)=[CH:49][CH:50]=2)[CH2:44][CH2:43][CH2:42]1)([CH3:37])([CH3:35])[CH3:36]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of triphenylphosphine (126 mg, 0.48 mmol) in CCl4 (2 mL) at 0° C. was added triethylamine (67 μL, 0.48 mmol) and TFA (13 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) was added and the temperature raised to 80° C. After 2 hours, 1,2-dichloroethane (1 mL) was added to aid solubility. The reaction mixture was stirred for a further 1 hour before cooling to RT. The solution was directly subjected to flash chromatography (SiO2, 40% ethyl acetate in cyclohexane) to give the title compound as an off-white solid (38 mg, 41%). LCMS (Method H): RT=4.20 min, [M+H]+=576.

Workup

waitAfter 2 hours
temperaturebefore cooling to RT

Sources & evidence

ORD record: ord-93c5cf2b60e9444da159b5333b5152de
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546376B2

Reaction notes

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