3-tert-butyl-4-chloro-N-(6-(2-chlorophenyl)-2-methoxy-3-nitropyridin-4-yl)-1-methyl-1H-pyrazole-5-carboxamide → N-(3-amino-6-(2-chlorophenyl)-2-methoxypyridin-4-yl)-3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxamide

HRID 570284Notes

Reaction equation

HRID 570284 reaction equation
[C:1]([C:5]1[C:9]([Cl:10])=[C:8]([C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[N:17]=[C:16]([O:27][CH3:28])[C:15]=2[N+:29]([O-])=O)=[O:12])[N:7]([CH3:32])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C>[NH2:29][C:15]1[C:16]([O:27][CH3:28])=[N:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])=[CH:19][C:14]=1[NH:13][C:11]([C:8]1[N:7]([CH3:32])[N:6]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[C:9]=1[Cl:10])=[O:12]

Participants

4

Reactant 2

HCID 674096383-tert-butyl-4-chloro-N-(6-(2-chlorophenyl)-2-methoxy-3-nitropyridin-4-yl)-1-methyl-1H-pyrazole-5-carboxamideHCID 178418361HCID 178418361, compound3×

Product 1

HCID 67411163N-(3-amino-6-(2-chlorophenyl)-2-methoxypyridin-4-yl)-3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A 2.25 L plastic coated Parr bottle was charged with 3-tert-butyl-4-chloro-N-(6-(2-chlorophenyl)-2-methoxy-3-nitropyridin-4-yl)-1-methyl-1H-pyrazole-5-carboxamide (55.30 g, 0.115 mol) and ethyl acetate (0.55 L). To the resulting slurry was added a slurry of 5% Pt(Sulfided)/C (2.80 g) in ethyl acetate (˜20 mL). The resulting mixture was agitated under 35-40 psi hydrogen gas, recharging with hydrogen gas as needed. After 3 h, hydrogen uptake ceased. The resulting mixture was filtered through CELITE to remove catalyst and the filter cake washed with ethyl acetate. The filtrate was concentrated to yield N-(3-amino-6-(2-chlorophenyl)-2-methoxypyridin-4-yl)-3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxamide as a off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ 1.42 (s, 9H), 3.98 (br. s., 2H), 4.06 (s, 3H), 4.15 (s, 3H), 7.27-7.35 (m, 2H), 7.44 (dd, J=7.83, 1.22 Hz, 1H), 7.55 (s, 1H), 7.63 (dd, J=7.58, 1.71 Hz, 1H), 8.54 (br. s., 1H)

Workup

  1. filtrationThe resulting mixture was filtered through CELITE
  2. customto remove catalyst
  3. washthe filter cake washed with ethyl acetate
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2985f869823d469989199cd83810a76c
Source dataset
uspto-grants-2015_05
Patent number
US09023846B2

Reaction notes

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