Potassium Cyanide → HCID 46241720, compound

HRID 2096156Notes

Reaction equation

HRID 2096156 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2([OH:35])[CH2:13][CH2:12][CH:11]([N:14]3[CH2:17][CH:16]([NH:18][C:19]([CH2:21][NH:22][C:23](=[O:34])[C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=4)=[O:20])[CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C-:36]#[N:37].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C.C(OCC)(=O)C.N.CO>[C:36]([C:2]1[N:7]=[CH:6][C:5]([C:8]2([OH:35])[CH2:13][CH2:12][CH:11]([N:14]3[CH2:17][CH:16]([NH:18][C:19]([CH2:21][NH:22][C:23](=[O:34])[C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:33])[F:32])[CH:25]=4)=[O:20])[CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)#[N:37]

Participants

8

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 46241719HCID 46241719, compound

Product 1

HCID 46241720HCID 46241720, compound

Reagents, catalysts & solvents 4

HCID 222AmmoniaSolvent2×HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

N-({1-[4-(6-fluoro-pyridin-3-yl)-4-hydroxy-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide 6a (70 mg, 0.14 mmol), KCN (Aldrich, 46 mg, 0.70 mmol) and 18-crown-6 (Aldrich, 190 mg, 0.70 mmol) in DMF (1 mL) were heated to 150° C. in a sealed tube overnight. The reaction solution was loaded on a silica gel column with a CombiFlash® system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford the title compound as a white solid.

Sources & evidence

ORD record
ord-3c371a5702024c55b56ea0bac6100708
Source dataset
uspto-grants-2013_05
Patent number
US08450304B2

Reaction notes

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