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 70986Notes

Reaction equation

HRID 70986 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-cce70f5eaa0b4c4d89590e8f6111bcdd
Source dataset
uspto-grants-2014_09
Patent number
US08822689B2

Reaction notes

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