Trifluoroacetic acid → 7-Dimethylamino-8-fluoro-4-[3-(3-hydroxymethyl-isoxazol-5-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1265789Notes

Reaction equation

HRID 1265789 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([N:14]([CH3:16])[CH3:15])[C:11]([F:17])=[CH:10][C:9]=1[NH:18][C:19](=[O:42])[CH2:20][C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]2[O:32][N:31]=[C:30]([CH2:33][O:34]C3CCCCO3)[CH:29]=2)[CH:23]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:15][N:14]([CH3:16])[C:12]1[C:11]([F:17])=[CH:10][C:9]2[NH:18][C:19](=[O:42])[CH2:20][C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]4[O:32][N:31]=[C:30]([CH2:33][OH:34])[CH:29]=4)[CH:23]=3)=[N:7][C:8]=2[CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86586834(RS)-[5-Dimethylamino-4-fluoro-2-(3-oxo-3-{3-[3-(tetrahydro-pyran-2-yloxymethyl)-isoxazol-5-yl]-phenyl}-propionylamino)-phenyl]-carbamic acid tert.-butyl ester

Product 1

HCID 186133837-Dimethylamino-8-fluoro-4-[3-(3-hydroxymethyl-isoxazol-5-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from (RS)-[5-dimethylamino-4-fluoro-2-(3-oxo-3-{3-[3-(tetrahydro-pyran-2-yloxymethyl)-isoxazol-5-yl]-phenyl}-propionylamino)-phenyl]-carbamic acid tert.-butyl ester (Example M40) (314 mg, 0.53 mmol) by treatment with TFA in CH2Cl2 according to the general procedure N. Obtained as a yellow solid (95 mg).

Sources & evidence

ORD record
ord-be756dd177484ed68397bddd8b073f2e
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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