HCID 86686154, compound → HCID 86686161, compound

HRID 1409754Notes

Reaction equation

HRID 1409754 reaction equation
[OH:1][NH:2][C:3](=[NH:7])[CH:4]([CH3:6])[CH3:5].[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]([CH:35]2[CH2:37][CH2:36]2)[C:17](=[O:34])[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=3)=[N:20][CH:19]=2)[CH2:12][CH2:11]1)#N>O1CCCC1.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH:35]1([N:16]([CH:13]2[CH2:14][CH2:15][N:10]([C:8]3[O:1][N:2]=[C:3]([CH:4]([CH3:6])[CH3:5])[N:7]=3)[CH2:11][CH2:12]2)[C:17](=[O:34])[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:28][CH:29]=3)=[N:20][CH:19]=2)[CH2:37][CH2:36]1

Participants

6

Reactant 2

HCID 86686154HCID 86686154, compoundHCID 178449908HCID 178449908, compound

Product 1

HCID 86686161HCID 86686161, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

0.5 M solution of zinc chloride in tetrahydrofuran (4.52 mL) is added dropwise at room temperature to a mixture of N-hydroxy-isobutyramidine (58 mg) and N-(1-cyano-piperidin-4-yl)-N-cyclopropyl-6-(4-methanesulfonyl-phenyl)-nicotinamide (160 mg) in ethyl acetate (8 mL). The reaction mixture is stirred at 50° C. for two days and cooled to room temperature. The precipitate is filtered off and heated to 100° C. for 1 h in a mixture of ethanol (6 mL) and glacial acetic acid (3 mL). The solvents are evaporated in vacuo and dichloromethane and 10% aqueous K2CO3 solution are added to the residue. The organic phase is separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is triturated with diethyl ether to give the title compound. LC (method 8): tR=1.51 min; Mass spectrum (ESI+): m/z=510 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate is filtered off
  3. temperatureheated to 100° C. for 1 h in a mixture of ethanol (6 mL) and glacial acetic acid (3 mL)
  4. customThe solvents are evaporated in vacuo and dichloromethane and 10% aqueous K2CO3 solution
  5. additionare added to the residue
  6. customThe organic phase is separated
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-54a11b82239d480db8a29a672d32cf93
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

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