Methanol → 1-[5-(Tert-butyldimethylsilanyloxymethyl)pyridin-2-yl]cyclopropylacetamide

HRID 589925Notes

Reaction equation

HRID 589925 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2(N)[CH2:18][CH2:17]2)=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:20]([O:23]C(=O)C)(=O)[CH3:21].CO.[N:29]1C=CC=CC=1>CN(C)C1C=CN=CC=1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([CH2:21][C:20]([NH2:29])=[O:23])[CH2:18][CH2:17]2)=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 594069831-[5-(Tert-butyldimethylsilanyloxymethyl)pyridin-2-yl]cyclopropylamine

Product 1

HCID 684316481-[5-(Tert-butyldimethylsilanyloxymethyl)pyridin-2-yl]cyclopropylacetamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

1-[5-(tert-Butyldimethylsilanyloxymethyl)pyridin-2-yl]cyclopropylamine (190 mg) was dissolved in pyridine (2 ml), acetic anhydride (0.13 ml) and 4-dimethylaminopyridine (17 mg) were added, and the mixture was stirred at room temperature for 4 hr. Methanol (2 ml) was added and the mixture was stirred for about 10 min. The solvent was evaporated, and the residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size L, elution solvent: hexane/ethyl acetate) to give the title compound (158 mg).

Workup

  1. stirringthe mixture was stirred for about 10 min
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size L, elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-edd45dd4352b411fa2ccbb5912266c33
Source dataset
uspto-grants-2016_01
Patent number
US09233969B2

Reaction notes

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