Trifluoroacetic acid → 3-[4-(1-Amino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid

HRID 1037407Notes

Reaction equation

HRID 1037407 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][C:16]1([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[C:35](=[O:36])[C:34]4[C:29](=[C:30]([C:37]([OH:39])=[O:38])[CH:31]=[CH:32][CH:33]=4)[O:28][C:27]=3[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:22][CH:21]=2)[CH2:19][CH2:18][CH2:17]1)=O)(C)(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[NH2:15][C:16]1([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[C:35](=[O:36])[C:34]4[C:29](=[C:30]([C:37]([OH:39])=[O:38])[CH:31]=[CH:32][CH:33]=4)[O:28][C:27]=3[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:24][CH:25]=2)[CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 670678653-[4-(1-tert-Butoxycarbonylamino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid

Product 1

HCID 670679903-[4-(1-Amino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acidYield 69.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

trifluoro-acetic acid: 3-[4-(1-tert-Butoxycarbonylamino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid (18 mg, 0.035 mmol) was treated with a solution of 25% TFA in DCM (4 mL) and stirred at RT for 1 h. The reaction mixture was diluted with toluene and concentrated in vacuo. The resultant residue was triturated with diethyl ether and DCM, and concentrated in vacuo to give the title compound as a light tan solid (10 mg, 54%). 1H NMR (400 MHz, DMSO-d6): δ 13.44 (bs, 1H), 8.44 (s, 3H), 8.28-8.23 (m, 2H), 7.57 (t, J=7.7 Hz, 1H), 7.48-7.36 (m, 5H), 7.33-7.27 (m, 4H), 2.64-2.53 (m, 2H), 2.51-2.42 (m, 2H), 2.18-2.05 (m, 1H), 1.85-1.73 (m, 1H). LCMS (Method E): RT=2.89 min, [M+H]+=412.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue was triturated with diethyl ether and DCM
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3130de00525c43d3b35e2a12ea873bf4
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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