Trifluoroacetic acid → 2-{4-[5-Chloro-2-(difluoromethoxy)phenyl]-5-methoxy-2-oxopyridin-1(2H)-yl}-4-methoxy-N-(2-methyl-3-oxo-2,3-dihydro-1H-indazol-6-yl)butanamide

HRID 57063Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:43][CH:44]([F:46])[F:45])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:38][CH2:39][O:40][CH3:41])[C:17]([NH:19][C:20]3[CH:28]=[C:27]4[C:23]([C:24](=[O:37])[N:25]([CH3:36])[N:26]4C(OC(C)(C)C)=O)=[CH:22][CH:21]=3)=[O:18])[C:10](=[O:42])[CH:9]=2)[CH:7]=1.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:43][CH:44]([F:46])[F:45])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:38][CH2:39][O:40][CH3:41])[C:17]([NH:19][C:20]3[CH:28]=[C:27]4[C:23]([C:24](=[O:37])[N:25]([CH3:36])[NH:26]4)=[CH:22][CH:21]=3)=[O:18])[C:10](=[O:42])[CH:9]=2)[CH:7]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 117622494tert-Butyl 6-[(2-{4-[5-chloro-2-(difluoromethoxy)phenyl]-5-methoxy-2-oxopyridin-1(2H)-yl}-4-methoxybutanoyl)amino]-2-methyl-3-oxo-2,3-dihydro-1H-indazole-1-carboxylate

Product 1

HCID 1176227792-{4-[5-Chloro-2-(difluoromethoxy)phenyl]-5-methoxy-2-oxopyridin-1(2H)-yl}-4-methoxy-N-(2-methyl-3-oxo-2,3-dihydro-1H-indazol-6-yl)butanamide

Procedure

132 mg (0.19 mmol) of tert-butyl 6-[(2-{4-[5-chloro-2-(difluoromethoxy)phenyl]-5-methoxy-2-oxopyridin-1(2H)-yl}-4-methoxybutanoyl)amino]-2-methyl-3-oxo-2,3-dihydro-1H-indazole-1-carboxylate (racemate) were hydrolysed with TFA according to General Method 2. The crude product was purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 48 mg (45% of theory)

Workup

customThe crude product was purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record: ord-46b46748bf9f4bcd9e40a8ff5e0cc428
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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