1,1-Dimethylhydrazine → 6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid N',N'-dimethyl-hydrazide

HRID 1516202Notes

Reaction equation

HRID 1516202 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][N:13]=2)=[C:8]([CH3:21])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:22][N:23]([CH3:25])[NH2:24].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>CN(C=O)C>[CH3:22][N:23]([CH3:25])[NH:24][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][C:12]([O:11][CH2:10][C:9]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=2[CH3:21])=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 59761,1-DimethylhydrazineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 665983356-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 498012616-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid N',N'-dimethyl-hydrazideYield 33.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.34 mmol) in DMF (5 mL) at room temperature under argon was added N,N-dimethylhydrazine (23 mg, 0.38 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (122 mg, 0.38 mmol) and N,N-diisopropylethylamine (223 mg, 1.7 mmol). After 15 h the reaction mixture was concentrated, diluted with water and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, dichloromethane:methanol 1:0 to 97.5:2.5) afforded the title compound (38 mg, 33%) as a colourless gum. MS: m/e=333.3 [M+H]+.

Workup

  1. concentrationAfter 15 h the reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (silica, dichloromethane:methanol 1:0 to 97.5:2.5)

Sources & evidence

ORD record
ord-68a7c8dbaa094c7a817ea90ce682040a
Source dataset
uspto-grants-2012_07
Patent number
US08227461B2

Reaction notes

Loading…