Isobutyraldehyde → HCID 57929944, compound

HRID 1930092Notes

Reaction equation

HRID 1930092 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:17]1[CH:18]=[N:19][C:20]([NH:23][NH2:24])=[N:21][CH:22]=1)[CH:14]=[CH:13][O:12]2.[CH:25](=O)[CH:26]([CH3:28])[CH3:27].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CC(O)=O.C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:17]1[CH:18]=[N:19][C:20]3[N:21]([C:25]([CH:26]([CH3:28])[CH3:27])=[N:24][N:23]=3)[CH:22]=1)[CH:14]=[CH:13][O:12]2

Participants

6

Reactant 3

HCID 6561IsobutyraldehydeHCID 12217721Iodo benzene diacetateHCID 57929856HCID 57929856, compound

Product 1

HCID 57929944HCID 57929944, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a flask was added 6-(2,4-difluorophenyl)-5-(2-hydrazinylpyrimidin-5-yl)imidazo[2,1-b]oxazole (0.120 g, 0.366 mmol) and DCM (8 mL). Isobutyraldehyde (0.026 g, 0.366 mmol) and HOAc (0.000021 mL, 0.000366 mmol) were added. The reaction mixture was stirred at ambient temperature for about 2 h. Then iodobenzene diacetate (0.124 g, 0.384 mmol) was added. The reaction mixture was stirred at ambient temperature for about 2 h. The crude material was purified by silica gel flash chromatography using a gradient of 0-20% MeOH in DCM to give the title compound (0.085 g, 61%): LC/MS (Table 1, Method a) Rt=2.62 min; MS m/z: 381.2 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for about 2 h
  2. customThe crude material was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-4b17322ad6e74675a614817804571533
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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