Water → HCID 178509194, compound

HRID 451529Notes

Reaction equation

HRID 451529 reaction equation
[C:1](/[N:3]=[C:4](\OC1C=CC=CC=1)/[N:5]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=1)[CH2:6][CH2:7][CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)#[N:2].O.[NH2:32][NH2:33].O>CO>[F:23][C:18]1[CH:17]=[C:16]([N:5]([CH2:6][CH2:7][CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[C:4]2[NH:3][C:1]([NH2:2])=[N:33][N:32]=2)[CH:21]=[CH:20][C:19]=1[F:22]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 178512390HCID 178512390, compound

Product 1

HCID 178509194HCID 178509194, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (Z)-phenyl N′-cyano-N-(3,4-difluorophenyl)-N-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)carbamimidate (73 mg, 176 μmol) in methanol (0.5 mL) was added hydrazine hydrate 25% in water (35.2 mg, 34.8 μl, 176 μmol). The reaction was stirred at room temperature over night. The solvent was evaporated under reduced pressure and the residue purified by column chromatography on silica gel using methylene chloride/methanol 19:1 (v/v) as eluent. The title compound was obtained as a light yellow viscous oil (46 mg, 74%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ce12e35b67c6487894c38cf1797118e2
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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