1-(5-Methyl-1,2-oxazol-3-yl)methanamine → HCID 67243207, compound

HRID 2422121Notes

Reaction equation

HRID 2422121 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][NH2:8])[CH:3]=1.[C:9]([N:13]1[C:17](=[O:18])[C:16](Cl)=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:14]1(=[O:27])=[O:26])([CH3:12])([CH3:11])[CH3:10]>>[C:9]([N:13]1[C:17](=[O:18])[C:16]([NH:8][CH2:7][C:4]2[CH:3]=[C:2]([CH3:1])[O:6][N:5]=2)=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:14]1(=[O:26])=[O:27])([CH3:12])([CH3:10])[CH3:11]

Participants

3

Reactant 2

HCID 27763061-(5-Methyl-1,2-oxazol-3-yl)methanamineHCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 67243207HCID 67243207, compoundYield 56%

Procedure

The title compound was prepared as described for Example 24 from 1 equivalent of [(5-methylisoxazol-3-yl)methyl]-amine, 2-tert-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide and 1 equivalent TEA with a reaction time of 45 mins. The mixture was evaporated and purified by silica gel column chromatography (Horizons Biotage) using 35% EtOAc in pentane as eluent to give the title compound (0.070 g, 56%). 1H NMR (500 MHz CDCl3): δ 7.52-7.48 (m, 2H), 7.46-7.41 (m, 3H), 5.73 (s, 1H), 5.66 (t, 1H), 5.07 (d, 2H), 2.39 (s, 3H), 1.74 (s, 9H); 13C N (125 MHz CDCl3): δ 170.7, 159.9, 159.4, 134.8, 131.6, 130.1, 128.9, 124.7, 109.3, 100.4, 61.9, 40.4, 27.8, 12.5; Mass Spectrum: M+H+ 376

Workup

  1. customThe title compound was prepared
  2. customThe mixture was evaporated
  3. custompurified by silica gel column chromatography (Horizons Biotage)

Sources & evidence

ORD record
ord-59bfcf56ef41442c9475f03fde264f99
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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