Pyridine → HCID 66706065, compound

HRID 1182826Notes

Reaction equation

HRID 1182826 reaction equation
ClCCl.[NH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[N:11][C:12]([N:15]2[C:20](=[O:21])[C:19]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]4[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:25][CH:24]=3)=[C:18]([CH2:37][CH2:38][CH2:39][CH3:40])[N:17]=[C:16]2[CH3:41])=[N:13][CH:14]=1.N1C=CC=CC=1.[C:48](Cl)(=[O:50])[CH3:49]>O>[CH2:37]([C:18]1[N:17]=[C:16]([CH3:41])[N:15]([C:12]2[N:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][NH:4][C:48](=[O:50])[CH3:49])=[CH:10][N:11]=2)[C:20](=[O:21])[C:19]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]#[N:36])=[CH:25][CH:24]=1)[CH2:38][CH2:39][CH3:40]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 66706189HCID 66706189, compound

Product 1

HCID 66706065HCID 66706065, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Process 3: To the dichloromethane (1 mL) solution of the crude product of 4′-{{1-[5-(3-aminopropoxy)pyrimidin-2-yl]-4-butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl}methyl}biphenyl-2-carbonitrile (45 mg), pyridine (9.7 mg, 0.123 mmol) and acetyl chloride (8.3 mg, 0.106 mmol) were added and stirred at room temperature overnight. The reaction mixture was added water, and extracted with ethyl acetate. The organic layer was combined, washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain N-{3-{2-{4-butyl-5-[(2′-cyanobiphenyl-4-yl)methyl]-2-methyl-6-oxopyrimidin-1 (6H)-yl}pyrimidin-5-yl oxy}propyl}acetamide (35 mg) as a crude product.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-f01d5e72d87a41aa8a578e4592698979
Source dataset
uspto-grants-2014_03
Patent number
US08664226B2

Reaction notes

Loading…