Trifluoroacetic acid → 2-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-N-[4-(5-oxo-2,5-dihydro-1H-pyrazol-3-yl)phenyl]propanamide

HRID 56954Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:39]#[N:40])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH3:37])[C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[N:28](C(OC(C)(C)C)=O)[NH:27][C:26](=[O:36])[CH:25]=4)=[CH:20][CH:19]=3)=[O:16])[C:10](=[O:38])[CH:9]=2)[CH:7]=1.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:39]#[N:40])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH3:37])[C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[NH:28][NH:27][C:26](=[O:36])[CH:25]=4)=[CH:20][CH:19]=3)=[O:16])[C:10](=[O:38])[CH:9]=2)[CH:7]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 117622739tert-Butyl 5-[4-({2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)phenyl]-3-oxo-2,3-dihydro-1H-pyrazole-1-carboxylate

Product 1

HCID 1176227422-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-N-[4-(5-oxo-2,5-dihydro-1H-pyrazol-3-yl)phenyl]propanamide

Procedure

110 mg (0.20 mmol) of tert-butyl 5-[4-({2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)phenyl]-3-oxo-2,3-dihydro-1H-pyrazole-1-carboxylate (racemate) (Example 2.3A) were hydrolysed with TFA according to General Method 2. Yield: 24 mg (27% of theory)

Sources & evidence

ORD record: ord-6ff066a89fa64e5293e94dddccd43b93
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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