Ethanol → HCID 57655973, compound

HRID 2041487Notes

Reaction equation

HRID 2041487 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][CH:10]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])=[CH:5][C:4]=1[F:19])#[N:2].CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C.C(O)C.[H][H]>C(O)(=O)C.O>[NH2:2][CH2:1][C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][CH:10]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])=[CH:5][C:4]=1[F:19]

Participants

7

Reactant 4

HCID 702EthanolHCID 493570RiboflavinHCID 57656528HCID 57656528, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57655973HCID 57655973, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Add 4-cyano-N-cycloheptyl-3-fluoro-benzamide (0.86 g, 3.3 mmol), 10% NYC (Degussa type E101, 250 mg), ethanol (25 mL), water (9 mL) and acetic acid (1 mL) to a pressure vessel under a nitrogen atmosphere. Pressurize the vessel to 50 psi with hydrogen, and stir the mixture for 0.5 h. Filter the mixture through Celite® and wash the cake with warm ethanol followed by dichloromethane under a nitrogen atmosphere. Concentrate the filtrate in vacuo to obtain the title compound as the acetic acid salt. Use SCX chromatography to obtain the title compound (805 mg, 92%). MS (ES+) m/z: 265.3 (M+H)+.

Workup

  1. filtrationFilter the mixture through Celite®
  2. washwash the cake with warm ethanol
  3. concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-5e5833ca5b0548eb9a5295a655be5588
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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