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

HRID 56998Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:42]#[N:43])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:39][CH3:40])[C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[N:30](C(OC(C)(C)C)=O)[NH:29][C:28](=[O:38])[CH:27]=4)=[CH:22][CH:21]=3)=[O:18])[C:10](=[O:41])[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:42]#[N:43])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:39][CH3:40])[C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[NH:30][NH:29][C:28](=[O:38])[CH:27]=4)=[CH:22][CH:21]=3)=[O:18])[C:10](=[O:41])[CH:9]=2)[CH:7]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 117622800tert-Butyl 5-[4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)phenyl]-3-oxo-2,3-dihydro-1H-pyrazole-1-carboxylate

Product 1

HCID 1176229432-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-N-[4-(5-oxo-2,5-dihydro-1H-pyrazol-3-yl)phenyl]butanamide

Procedure

17 mg (purity 70%, 0.02 mmol) of tert-butyl 5-[4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)phenyl]-3-oxo-2,3-dihydro-1H-pyrazole-1-carboxylate (racemate) were hydrolysed with TFA according to General Method 2. Yield: 8 mg (78% of theory)

Sources & evidence

ORD record: ord-843dcaf77a0342c8a97a1190d509fcad
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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