Acetic Acid → HCID 19975548, compound

HRID 2226562Notes

Reaction equation

HRID 2226562 reaction equation
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][N:15]=3)[CH:10]=2)[O:5][CH2:4][CH2:3]1.[C:23](O)(=[O:25])[CH3:24].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:23](=[O:25])[CH3:24])=[CH:16][N:15]=3)[CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 19975483HCID 19975483, compound

Product 1

HCID 19975548HCID 19975548, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.81 g (10 mmol) of 2-[2-(4,4-dimethylchroman-6-yl)ethynyl]-5-hydroxymethylpyridine, 600 mg (10 mmol) of glacial acetic acid, 2.06 g (10 mmol) of dicyclohexylcarbodiimide and 460 mg (3.765 mmol) of 4-dimethylaminopyridine in 150 ml methylene chloride is stirred at room temperature for 48 hours. The reaction mixture is then filtered and the residue washed with 50 ml of methylene chloride. The filtrate is then concentrated in vacuo and the residue is purified by chromatography followed by recrystallization to give the title compound.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. washthe residue washed with 50 ml of methylene chloride
  3. concentrationThe filtrate is then concentrated in vacuo
  4. customthe residue is purified by chromatography
  5. customfollowed by recrystallization

Sources & evidence

ORD record
ord-8d128204a07a45f5bf8b750b2af14e45
Source dataset
uspto-grants-1994_09
Patent number
US05348972

Reaction notes

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