1,1-Dimethylhydrazine → HCID 46929325, compound

HRID 1514732Notes

Reaction equation

HRID 1514732 reaction equation
[OH:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:4]=1[CH2:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][N:17]=1.[CH3:25][N:26]([CH3:28])[NH2:27].F[B-](F)(F)F.C[N+](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:25][N:26]([CH3:28])[NH:27][C:20](=[O:22])[C:19]1[CH:23]=[CH:24][C:16]([O:15][CH2:14][C:4]2[C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)=[N:6][O:7][C:3]=2[CH2:2][OH:1])=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 59761,1-DimethylhydrazineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66718204HCID 66718204, compound

Product 1

HCID 46929325HCID 46929325, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(5-hydroxymethyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinic acid (70 mg, 0.21 mmol) in DMF (5 mL) was added N,N-dimethylhydrazine (18 mg, 0.30 mmol), N,N,N′,N′-tetramethyl-O-(benzotriazole-1-yl)-uronium tetrafluoroborate (96 mg, 0.30 mmol) and N,N-diisopropyl ethylamine (0.15 mL, 0.84 mmol). The reaction mixture was stirred overnight at room temperature. After evaporation of the solvent the residue was partitioned (ethyl acetate/aqueous saturated sodium bicarbonate solution) and the organic phase was dried (Na2SO4), filtered and concentrated. Chromatography (silica, dichloromethane:methanol=100:0 to 97:3) afforded the title compound (49 mg, 62%) as a white solid. MS: m/e=370.1 [M+H]+.

Workup

  1. customAfter evaporation of the solvent the residue
  2. customwas partitioned (ethyl acetate/aqueous saturated sodium bicarbonate solution)
  3. dry with materialthe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3ad8f6a9f82a42f6b600c12cb6f05d9d
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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