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

HRID 1037268Notes

Reaction equation

HRID 1037268 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C:15]1([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[C:30](=[O:31])[C:29]4[CH:32]=[CH:33][C:34](N)=[CH:35][C:28]=4[O:27][C:26]=3[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:21][CH:20]=2)[CH2:18][CH2:17][CH2:16]1)(C)(C)C>ClCCl>[NH2:14][C:15]1([C:19]2[CH:20]=[CH:21][C:22]([C:25]3[C:30](=[O:31])[C:29]4[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=4[O:27][C:26]=3[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:23][CH:24]=2)[CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67067858{1-[4-(7-Amino-4-oxo-2-phenyl-4H-1-benzopyran-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510297713-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-1-benzopyran-4-oneYield 145.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA: To a solution of {1-[4-(7-amino-4-oxo-2-phenyl-4H-1-benzopyran-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (12.2 mg, 0.03 mmol) in dichloromethane (1 mL) was added TFA (1 mL) and the mixture was stirred at RT for 1 hour. The reaction mixture was concentrated in vacuo to give a white solid (16.0 mg, 100%). 1H-NMR (400 MHz, D2O) δ 8.02 (d, 1H), 7.76 (dd, 2H), 7.55 (d, 2H), 7.42 (dd, 2H), 7.28-7.34 (m, 3H), 7.17-7.22 (m, 3H) 2.60-2.67 (m, 2H), 2.44-2.52 (m, 2H), 2.04-2.08 (m, 1H), 1.80-1.83 (m, 1H). LCMS (Method I): RT=4.50 min, [M+H]+=368

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-8aeb11ea5aa34d9298df8316b80522ef
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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