Potassium Carbonate → N-[1-(2-Cyclopropyl-1-methylethyl)piperidin-4-yl]-6-(3-fluorophenyl)nicotinamide

HRID 602087

Reaction equation

HRID 602087 reaction equation
[CH:1]1([CH2:4][C:5](=O)[CH3:6])[CH2:3][CH2:2]1.[F:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:29]=[CH:28][C:18]([C:19]([NH:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[O:20])=[CH:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[K+].[K+]>C(O)C.C(O)(=O)C.CS(C)=O.C1COCC1>[CH:1]1([CH2:4][CH:5]([N:25]2[CH2:24][CH2:23][CH:22]([NH:21][C:19](=[O:20])[C:18]3[CH:28]=[CH:29][C:15]([C:11]4[CH:12]=[CH:13][CH:14]=[C:9]([F:8])[CH:10]=4)=[N:16][CH:17]=3)[CH2:27][CH2:26]2)[CH3:6])[CH2:3][CH2:2]1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 5370251-Cyclopropylpropan-2-oneHCID 5049666Sodium triacetoxyborohydrideHCID 672679066-(3-fluorophenyl)-N-(piperidin-4-yl)nicotinamide

Product 1

HCID 59743699N-[1-(2-Cyclopropyl-1-methylethyl)piperidin-4-yl]-6-(3-fluorophenyl)nicotinamide

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-cyclopropylpropan-2-one (0.2 mL, 0.08 mmol in 1:1 THF:DMSO) was added 6-(3-fluorophenyl)-N-(piperidin-4-yl)nicotinamide (in 1:1 THF:DMSO, 0.2 mL, 0.08 mmol), sodium triacetoxyborohydride dispersion (0.33 mL, 2.5 eq, in 1:1 THF:DMSO) and glacial acetic acid (0.01 mL). The reaction mixture was stirred at room temperature for 16-24 h and then aqueous K2CO3 (3 M, 0.2 mL) and ethanol (0.55 mL) was added. The reaction was shaken for 30 min and then the mixture was filtered and the filtrate concentrated and the residue purified by RP-HPLC to give the desired product. LC/MS=382.4 (M+H) observed, 382.23 expected.

Workup

  1. stirringThe reaction was shaken for 30 min
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate concentrated
  4. customthe residue purified by RP-HPLC

Sources & evidence

ORD record
ord-3768ad9dae2347b9ab440a2bbb884ccf
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Linked notes

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