Trifluoroacetic acid → 2-[2-Bromo-5-(propionylamino)phenyl]-5-n-butyl-2,4-dihydro-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one

HRID 1198697Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[CH2:10][CH3:11])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[S:32](=[O:39])(=[O:38])[NH:33]C(C)(C)C)=[CH:22][C:21]=2[F:40])[C:15]([CH2:41][CH2:42][CH2:43][CH3:44])=[N:14]1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[CH2:10][CH3:11])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[S:32](=[O:39])(=[O:38])[NH2:33])=[CH:22][C:21]=2[F:40])[C:15]([CH2:41][CH2:42][CH2:43][CH3:44])=[N:14]1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 19102787HCID 19102787, compound

Product 1

HCID 103490632-[2-Bromo-5-(propionylamino)phenyl]-5-n-butyl-2,4-dihydro-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-oneYield 88%

Procedure

The title compound was prepared from 2-[2-bromo-5-(propionylamino)-phenyl]-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step E) by reaction with trifluoroacetic acid in the presence of anisole according to the procedure of Example 28, Step G, giving an 88% yield of the title compound as an off-white foam; homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 630,632 (M+1)+.

Sources & evidence

ORD record: ord-1b8aed257f6e4ff58bee25f13dd52383
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05281614

Reaction notes

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