tert-Butyl 6-amino-2-methyl-3-oxo-2,3-dihydro-1H-indazole-1-carboxylate → 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

HRID 56635Notes

Reaction equation

HRID 56635 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20]#[N:21])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH3:18])[C:15]([OH:17])=O)[C:10](=[O:19])[CH:9]=2)[CH:7]=1.[NH2:22][C:23]1[CH:31]=[C:30]2[C:26]([C:27](=[O:40])[N:28]([CH3:39])[N:29]2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:25][CH:24]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20]#[N:21])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH3:18])[C:15]([NH:22][C:23]3[CH:31]=[C:30]4[C:26]([C:27](=[O:40])[N:28]([CH3:39])[N:29]4[C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])=[CH:25][CH:24]=3)=[O:17])[C:10](=[O:19])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 117622556tert-Butyl 6-amino-2-methyl-3-oxo-2,3-dihydro-1H-indazole-1-carboxylateHCID 1176228502-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoic acid

Product 1

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

Procedure

89 mg (purity 83%, 0.24 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoic acid (racemate) and 1.1 eq. of tert-butyl 6-amino-2-methyl-3-oxo-2,3-dihydro-1H-indazole-1-carboxylate were reacted according to General Method 5A. The crude product was purified by preparative HPLC (Reprosil C18, water/methanol gradient). Yield: 75 mg (56% of theory)

Workup

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

Sources & evidence

ORD record
ord-67b6f3d2d475483db7e6a1e63800a19c
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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