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

HRID 56982Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=2[C:40]#[N:41])=[CH:4][C:5](=[O:32])[N:6]([CH:8]([CH3:31])[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:22](C(OC(C)(C)C)=O)[NH:21][C:20](=[O:30])[CH:19]=3)=[CH:14][CH:13]=2)=[O:10])[CH:7]=1.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[C:3]([C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=2[C:40]#[N:41])=[CH:4][C:5](=[O:32])[N:6]([CH:8]([CH3:31])[C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[NH:22][NH:21][C:20](=[O:30])[CH:19]=3)=[CH:16][CH:17]=2)=[O:10])[CH:7]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 117622708tert-Butyl 5-[4-({2-[5-chloro-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 1176228382-[5-Chloro-4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-N-[4-(5-oxo-2,5-dihydro-1H-pyrazol-3-yl)phenyl]propanamide

Procedure

17.8 mg (purity 78%, 0.02 mmol) of tert-butyl 5-[4-({2-[5-chloro-4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)phenyl]-3-oxo-2,3-dihydro-1H-pyrazole-1-carboxylate (racemate) (Example 12.2A) were reacted with TFA according to General Method 2. Yield: 6 mg (55% of theory)

Sources & evidence

ORD record: ord-0de00aa26bc040baa1467604714cf719
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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