Nicotinic Acid → HCID 178454039, compound

HRID 1445362Notes

Reaction equation

HRID 1445362 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22](O)=[O:23])[CH:17]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([NH:15][C:22]([C:18]2[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=2)=[O:23])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 938Nicotinic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 178419079HCID 178419079, compound

Product 1

HCID 178454039HCID 178454039, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 ml of a N,N-dimethylformamide solution containing 1 g of N-tert-butoxycarbonyl-trans-1,4-cyclohexanediamine, 632 mg of 3-pyridinecarboxylic acid, 1.07° g of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide and 757 mg of 1-hydroxybenzotriazole was stirred at room temperature for 24 hours. To the reaction mixture was added an aqueous saturated sodium hydrogencarbonate solution and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was washed with diethyl ether to obtain N-tert-butoxycarbonyl-trans-4-(3-pyridylcarbonylamino)cyclohexylamine. A mixture comprising 1.27 g of this compound and 13 ml of 15% hydrochloric acid-ethanol solution was stirred at 50° C. for 2 hours. After cooling, precipitates were filtered and washed with diethyl ether to obtain 1.12 g of trans-4-(3-pyridylcarbonylamino)cyclohexylamine.dihydrochloride (Reference Example 10-2 in Table 11).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-22b082a94e9d4670ab026dcceb5c75ba
Source dataset
uspto-grants-2010_02
Patent number
US07666869B2

Reaction notes

Loading…