1,1-Dimethylhydrazine → 2-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid N',N'-dimethyl-hydrazide

HRID 1923617Notes

Reaction equation

HRID 1923617 reaction equation
[CH2:1]([C:5]1[C:9](/[CH:10]=[CH:11]/[C:12]2[S:13][C:14]([C:18]([OH:20])=O)=[C:15]([CH3:17])[N:16]=2)=[C:8]([CH3:21])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH3:53][N:54]([CH3:56])[NH2:55]>CN(C=O)C>[CH3:53][N:54]([CH3:56])[NH:55][C:18]([C:14]1[S:13][C:12](/[CH:11]=[CH:10]/[C:9]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=2[CH3:21])=[N:16][C:15]=1[CH3:17])=[O:20]

Participants

6

Reactant 4

HCID 59761,1-DimethylhydrazineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 595685392-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid

Product 1

HCID 595685222-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid N',N'-dimethyl-hydrazideYield 44.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(E)-2-(3-butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid (90 mg, 0.29 mmol) in DMF (5 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (104 mg, 0.32 mmol), N,N-diisopropyl ethyl amine (250 μL, 1.47 mmol) and 1,1-dimethylhydrazine (0.03 mL, 0.39 mmol). The resulting reaction mixture was stirred for 1 h. The reaction mixture was then evaporated and purification by chromatography (silica, 0 to 2% methanol in dichloromethane) afforded the title compound (45 mg, 44%) as a white solid. MS: m/e=349.3 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was then evaporated
  3. custompurification by chromatography (silica, 0 to 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-439fbc0254394b628b3a0022397f01a2
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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