Trifluoroacetic acid → HCID 178487601, compound

HRID 2202291Notes

Reaction equation

C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([NH:20][C:21]([C@@H:23]2[N:32]([C:33]([C@H:35]3[CH2:38][C@H:37]([CH2:39][C:40]([O:42]C(C)(C)C)=[O:41])[CH2:36]3)=[O:34])[CH2:31][CH2:30][C:29]3[N:28]=[C:27]([O:47][CH3:48])[CH:26]=[CH:25][C:24]2=3)=[O:22])[CH:12]=[C:13]2[C:17]=1[C:16]([CH3:19])([CH3:18])[CH2:15][CH2:14]2>>[F:8][C:9]1[CH:10]=[C:11]([NH:20][C:21]([C@@H:23]2[N:32]([C:33]([C@H:35]3[CH2:38][C@H:37]([CH2:39][C:40]([OH:42])=[O:41])[CH2:36]3)=[O:34])[CH2:31][CH2:30][C:29]3[N:28]=[C:27]([O:47][CH3:48])[CH:26]=[CH:25][C:24]2=3)=[O:22])[CH:12]=[C:13]2[C:17]=1[C:16]([CH3:19])([CH3:18])[CH2:15][CH2:14]2

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178487607HCID 178487607, compound

Product 1

HCID 178487601HCID 178487601, compoundYield 84%

Conditions

Temperature: 0 °C

Procedure

Cooled TFA (2 mL) was added to tert-butyl 2-(trans-3-((R)-5-((7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)carbamoyl)-2-methoxy-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclobutyl)acetate (150 mg, 0.27 mmol) at 0° C., and the mixture was stirred at 0° C. for 30 min. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (solvent gradient; 50→100% ethyl acetate/hexane) to give the title compound (113 mg, 0.222 mmol, 84%) as a white solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (solvent gradient; 50→100% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-23399f7281ee46579ec24b7dc85cf0a9
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365520B2

Reaction notes

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