Trifluoroacetic acid → 7-Amino-3-[4-(1-amino-cyclobutyl)-phenyl]-2-phenyl-1-benzopyran-4-one

HRID 1037271Notes

Reaction equation

HRID 1037271 reaction equation
C(O)(C(F)(F)F)=O.NC1(C2C=CC(C3C(=O)C4C=CC=CC=4OC=3C3C=CC=CC=3)=CC=2)CCC1.C(OC(=O)[NH:42][C:43]1([C:47]2[CH:52]=[CH:51][C:50]([C:53]3[C:58](=[O:59])[C:57]4[CH:60]=[CH:61][C:62]([NH2:64])=[CH:63][C:56]=4[O:55][C:54]=3[C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:49][CH:48]=2)[CH2:46][CH2:45][CH2:44]1)(C)(C)C>>[NH2:64][C:62]1[CH:61]=[CH:60][C:57]2[C:58](=[O:59])[C:53]([C:50]3[CH:51]=[CH:52][C:47]([C:43]4([NH2:42])[CH2:46][CH2:45][CH2:44]4)=[CH:48][CH:49]=3)=[C:54]([C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=3)[O:55][C:56]=2[CH:63]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 510297713-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-1-benzopyran-4-oneHCID 67067858{1-[4-(7-Amino-4-oxo-2-phenyl-4H-1-benzopyran-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510297727-Amino-3-[4-(1-amino-cyclobutyl)-phenyl]-2-phenyl-1-benzopyran-4-oneYield 156.9%

Procedure

TFA: Following the procedure used to make 3-[4-(1-amino-cyclobutyl)-phenyl]-2-phenyl-1-benzopyran-4-one, {1-[4-(7-amino-4-oxo-2-phenyl-4H-1-benzopyran-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (6.3 mg, 0.017 mmol) was reacted to give the title compound as a yellow solid (10.2 mg, 100%). 1H-NMR (400 MHz, D2O) δ 7.30 (d, 1H), 7.05-7.18 (m, 4H), 6.85 (dd, 2H), 6.59-6.65 (m, 4H) 5.65 (s, 1H) 2.33-2.47 (m, 4H), 1.95-2.02 (m, 1H), 1.52-1.59 (m, 1H). LCMS (Method I): RT=3.97 min, [M+H]+=384.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-0c29e7f50f0647cbb44ee3e6bb0eb675
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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