1-[6-(4-Fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone → 3-(Dimethylamino)-1-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]prop-2-en-1-one

HRID 1783809Notes

Reaction equation

HRID 1783809 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16](=[O:18])[CH3:17])[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1>COC(OC)N(C)C>[CH3:13][N:14]([CH3:15])[CH:10]=[CH:17][C:16]([C:15]1[N:14]2[C:10]([O:11][CH:12]=[CH:13]2)=[N:9][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:18]

Participants

3

Reactant 1

HCID 167264821-[6-(4-Fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone

Product 1

HCID 675198943-(Dimethylamino)-1-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]prop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A solution of 1-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone (0.0374 g, 0.000153 mol) in N,N-dimethylformamide dimethyl acetal (3.0 ml) was heated to 100° C. for 24 hrs. HPLC showed complete consumption of the starting material. The volatiles were removed in vacuo, yielding a brown solid (0.046 g, quantitative). M.p.=187-189° C.; 300 MHz 1H NMR (CDCl3) δ 8.03 (s, 1H), 7.72-7.64 (m, 3H), 7.46 (s, 1H), 7.13-7.10 (m, 2H), 5.19 (d, J=12.5 Hz, 1H), 3.07 (bs, 3H), 2.55 (bs, 3H). LCMS: 300 [M+H]. Calc. for C16H14FN3O2: C, 64.21; H, 4.71; N, 14.04. Found C, 64.22; H, 4.31; N, 14.10.

Workup

  1. customconsumption of the starting material
  2. customThe volatiles were removed in vacuo
  3. customyielding a brown solid (0.046 g, quantitative)

Sources & evidence

ORD record
ord-790c0f95a01d44d585155e8649d27c2e
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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