2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid → HCID 178454439, compound

HRID 57077

Reaction equation

HRID 57077 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]#[N:24])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH3:21])[C:17](O)=[O:18])[C:10](=[O:22])[CH:9]=2)[CH:7]=1.[Cl:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([NH2:35])[CH:33]=2)[NH:28][N:27]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]#[N:24])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH3:21])[C:17]([NH:35][C:32]3[CH:33]=[C:34]4[C:29](=[CH:30][CH:31]=3)[NH:28][N:27]=[C:26]4[Cl:25])=[O:18])[C:10](=[O:22])[CH:9]=2)[CH:7]=1.[Cl:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([NH2:35])[CH:33]=2)[NH:28][N:27]=1

Participants

4

Reactant 2

HCID 1176225692-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acidHCID 178507360HCID 178507360, compound

Product 2

HCID 178454439HCID 178454439, compoundHCID 178507360HCID 178507360, compound

Procedure

In two batches, a total of 242 mg (0.68 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid (racemate) and 404 mg (purity 31%, 0.75 mmol, 1.1 eq.) of 3-chloro-1H-indazole-5-amine were reacted according to General Method 1. The combined crude products were purified by repeated preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 18 mg (purity 94%, 13% of theory) of the title compound Example 196 and 65 mg (55% of theory) of the title compound Example 197, which was isolated as a by-product due to the starting material 3-chloro-1H-indazole-5-amine employed being contaminated with 1H-indazole-5-amine.

Workup

  1. customwere purified

Sources & evidence

ORD record
ord-cd552e811f9843119bf5be8304133bc3
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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