Pyridine → HCID 488732, compound

HRID 912607Notes

Reaction equation

HRID 912607 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:13]=[C:12]([CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])[N:11]=[C:10]([NH:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)[N:9]=1.[C:32](Cl)(=[O:40])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>C(Cl)Cl>[Cl:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:15]=1[CH2:14][C:12]1[N:11]=[C:10]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]#[N:29])=[CH:30][CH:31]=2)[N:9]=[C:8]([NH:7][C:32](=[O:40])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8124Octanoyl chloride2×HCID 486363HCID 486363, compound

Product 1

HCID 488732HCID 488732, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Pyridine (0.014 mol) was added to a mixture of 4-[[4-amino-6-[(2,6-dichlorophenyl)-methyl]-2-pyrimidinyl]amino]benzonitrile (0.0013 mol) in CH2Cl2. A solution of octanoyl chloride (1.5 equiv) in CH2Cl2 (0.5 ml) was added dropwise. The mixture was stirred at room temperature for 2 hours. More octanoyl chloride (3.5 equiv) in CH2Cl2 was added dropwise. The mixture was stirred. The solvent was then evaporated. The residue was treated with a saturated aqueous NaHCO3 solution and the mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent was evaporated to give the crude product. The residue was recrystallized from CHCl3 and hexane, yielding 0.443 g (68.6%) of N-[6-[(2,6-dichloro-phenyl)methyl]-2-[(4-cyano-phenyl)amino]-4-pyrimidinyl]octanamide (comp. 17; mp. 135-137° C.).

Workup

  1. stirringThe mixture was stirred
  2. customThe solvent was then evaporated
  3. additionThe residue was treated with a saturated aqueous NaHCO3 solution
  4. extractionthe mixture was extracted with CH2Cl2
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customto give the crude product
  9. customThe residue was recrystallized from CHCl3 and hexane

Sources & evidence

ORD record
ord-51b44ce7d5174d44a60a6a42479f83bb
Source dataset
uspto-grants-2011_09
Patent number
US08026248B2

Reaction notes

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