Trifluoroacetic acid → HCID 68278540, compound

HRID 1423270Notes

Reaction equation

HRID 1423270 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([C:19]4[N:23]=[C:22]([CH3:24])[O:21][N:20]=4)=[CH:14][CH:15]=3)[N:10]=[C:9]2[S:25][CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([C:19]4[N:23]=[C:22]([CH3:24])[O:21][N:20]=4)=[CH:14][CH:15]=3)[N:10]=[C:9]2[S:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68277899HCID 68277899, compound

Product 1

HCID 68278540HCID 68278540, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-(3-(4-fluorophenyl)-7-(5-methyl-1,2,4-oxadiazol-3-yl)-4-oxo-3,4-dihydroquinazolin-2-ylthio)acetate (10C, 25 mg, 0.0534 mmol), was treated with 5 mL 20% TFA in DCM for 14 hours. The reaction was concentrated and purified by reverse phase prep LC to yield 2-(3-(4-fluorophenyl)-7-(5-methyl-1,2,4-oxadiazol-3-yl)-4-oxo-3,4-dihydroquinazolin-2-ylthio)acetic acid (10, 15.6 mg, 64% yield). MS (M+H)=413.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by reverse phase prep LC

Sources & evidence

ORD record
ord-b7513e5f5b7b42619b79923c3da2f649
Source dataset
uspto-grants-2015_01
Patent number
US08927559B2

Reaction notes

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