Trifluoroacetic acid → 3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one

HRID 1037156Notes

Reaction equation

HRID 1037156 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([F:29])[CH:25]=4)[O:20][C:19]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([F:29])[CH:25]=4)[O:20][C:19]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67067635{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of {1-[4-(6-fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (22 mg, 0.045 mmol) in DCM (4 mL) was added TFA (1 mL). The mixture was stirred at RT for 1 h and then directly loaded onto an SCX cartridge (2 g, pre-wet using DCM). Impurities were removed by eluting with MeOH:DCM (1:1) and product eluted using NH3 solution (2M in MeOH):DCM (1:1) to give the title compound (14 mg, 82%). LCMS (Method F): RT=9.03 min, [M+H]+=386. 1H NMR (400 MHz, CDCl3): δ 7.92 (dd, J=8.3 and 3.2 Hz, 1H), 7.55 (dd, J=9.5 and 4.7 Hz, 1H), 7.47-7.32 (m, 6H), 7.29 (d, J=7.9 Hz, 2H), 7.19 (d, J=8.3 Hz, 2H), 2.61-2.50 (m, 2H), 2.22-2.00 (m, 3H), 1.82-1.69 (m, 1H).

Workup

  1. customImpurities were removed
  2. washby eluting with MeOH:DCM (1:1) and product
  3. washeluted

Sources & evidence

ORD record
ord-266aa624e1f44ec89dd25503ca39404d
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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