Trifluoroacetic acid → 2-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-N-(2-methyl-3-oxo-2,3-dihydro-1H-indazol-6-yl)propanamide

HRID 56964Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:38]#[N:39])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH3:36])[C:15]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([C:22](=[O:35])[N:23]([CH3:34])[N:24]4C(OC(C)(C)C)=O)=[CH:20][CH:19]=3)=[O:16])[C:10](=[O:37])[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:38]#[N:39])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH3:36])[C:15]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([C:22](=[O:35])[N:23]([CH3:34])[NH:24]4)=[CH:20][CH:19]=3)=[O:16])[C:10](=[O:37])[CH:9]=2)[CH:7]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 117622856tert-Butyl 6-({2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)-2-methyl-3-oxo-2,3-dihydro-1H-indazole-1-carboxylate

Product 1

HCID 1176229022-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-N-(2-methyl-3-oxo-2,3-dihydro-1H-indazol-6-yl)propanamide

Procedure

75 mg (0.14 mmol) of tert-butyl 6-({2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)-2-methyl-3-oxo-2,3-dihydro-1H-indazole-1-carboxylate (racemate) (Example 2.7A) were hydrolysed with TFA according to General Method 2. Yield: 37 mg (60% of theory)

Sources & evidence

ORD record: ord-394eb7fb37b74eafbc613f97be7c0d10
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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