Methanol → HCID 66620668, compound

HRID 415775Notes

Reaction equation

HRID 415775 reaction equation
[C:1]([C:3]([CH3:34])([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)[CH2:4][N:5]1[C:13]([O:14][CH3:15])=[C:12]2[C:7]([CH:8]=[C:9]([C:16](OC)=O)[CH:10]=[CH:11]2)=[N:6]1)#[N:2].[OH-:35].[NH4+:36].[CH3:37]O>>[CH3:16][C:9]1[C:8]2[C:7]([CH:12]=[C:11]([C:37]([NH2:36])=[O:35])[CH:10]=1)=[N:6][N:5]([CH2:4][C:3]([C:1]#[N:2])([CH3:34])[NH:20][C:21](=[O:33])[C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([F:31])([F:32])[F:30])=[CH:24][CH:23]=1)[C:13]=2[O:14][CH3:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 66620278HCID 66620278, compound

Product 1

HCID 66620668HCID 66620668, compound

Procedure

A solution of methyl 2-[2-cyano-2-methyl-2-(4-trifluoromethoxybenzoylamino)ethyl]-3-methoxy-2H-indazole-6-carboxylate (50 mg, described in Example 127) in methanol (3 mL) was stirred with ammonium hydroxide (1.5 mL) at room temperature for 8 days. The reaction mixture was 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 (3 mg). MS (ES): M/Z [M+H]=462. 1H NMR: (400 MHz, METHANOL-d4): 1.81 (s, 3H), 4.32 (s, 3H), 4.82 (d, 1H), 5.08 (d, J=14.0 Hz, 1H), 7.38 (dd, J=9.0, 1.4 Hz, 1H), 7.42 (d, J=8.6 Hz, 2H), 7.90 (d, J=9.0 Hz, 1H), 7.97 (d, J=8.9 Hz, 2H) and 7.99 (s, 1H). 19F NMR (376 MHz, METHANOL-d4): −59.8 (s, 3F).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto yield a residue that
  3. customwas purified by chromatography (SiO2, heptane/EA)

Sources & evidence

ORD record
ord-9ac8f3550945499087016830f162b438
Source dataset
uspto-grants-2012_01
Patent number
US08088801B2

Reaction notes

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