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 2062017Notes

Reaction equation

HRID 2062017 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 128 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-c9cce43a695b49c5898c674267112ada
Source dataset
uspto-grants-2012_10
Patent number
US08283475B2

Reaction notes

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