N-[1-cyano-2-(3-methoxy-6-nitro-2H-indazol-2-yl)-1-methylethyl]-4-trifluoromethoxybenzamide → N-[2-(6-Amino-3-methoxy-2H-indazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide

HRID 1257021Notes

Reaction equation

HRID 1257021 reaction equation
[C:1]([C:3]([NH:20][C:21](=[O:33])[C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=1)([CH3:19])[CH2:4][N:5]1[C:13]([O:14][CH3:15])=[C:12]2[C:7]([CH:8]=[C:9]([N+:16]([O-])=O)[CH:10]=[CH:11]2)=[N:6]1)#[N:2]>[Pd].CO>[NH2:16][C:9]1[CH:10]=[CH:11][C:12]2[C:7]([CH:8]=1)=[N:6][N:5]([CH2:4][C:3]([NH:20][C:21](=[O:33])[C:22]1[CH:23]=[CH:24][C:25]([O:28][C:29]([F:32])([F:30])[F:31])=[CH:26][CH:27]=1)([C:1]#[N:2])[CH3:19])[C:13]=2[O:14][CH3:15]

Participants

4

Reactant 1

HCID 66620221N-[1-cyano-2-(3-methoxy-6-nitro-2H-indazol-2-yl)-1-methylethyl]-4-trifluoromethoxybenzamide

Product 1

HCID 66620247N-[2-(6-Amino-3-methoxy-2H-indazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamideYield 64.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-[1-cyano-2-(3-methoxy-6-nitro-2H-indazol-2-yl)-1-methylethyl]-4-trifluoromethoxybenzamide (30 mg) described in Example 139 and palladium on charcoal in methanol (2 mL) were stirred at room temperature under hydrogen for 2.5 hours. The reaction mixture was filtered through a plug of Celite® and concentrated under reduced pressure to yield a residue that was purified by chromatography (SiO2, heptane/EA) to afford the title compound as a white solid (18 mg, 64%). MS (ES): M/Z [M+H]=434. 1H NMR: (400 MHz, CHLOROFORM-d): 1.88 (s, 3H), 4.38 (s, 3H), 4.41 (d, 1H), 4.72 (d, J=14.2 Hz, 1H), 6.48 (dd, J=9.0, 1.8 Hz, 1H), 6.53 (d, J=1.2 Hz, 1H), 7.31 (d, J=8.3 Hz, 2H), 7.55 (d, J=9.0 Hz, 1H), 7.98 (d, J=8.8 Hz, 2H) and 9.43 (s, 1H). 19F NMR (376 MHz, CHLOROFORM-d): −58.0 (s, 3F).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite®
  2. concentrationconcentrated under reduced pressure
  3. customto yield a residue that
  4. customwas purified by chromatography (SiO2, heptane/EA)

Sources & evidence

ORD record
ord-42135831dc87480f8691e711d43687dc
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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