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 415773Notes

Reaction equation

HRID 415773 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-6ca92a82474b4995ae4d5bea7f0e5498
Source dataset
uspto-grants-2012_01
Patent number
US08088801B2

Reaction notes

Loading…