4-Butoxybenzoic acid → N'-(4-butoxybenzoyl)-4-(3-dimethylaminopyrrolidin-1-yl)benzohydrazide

HRID 2251297

Reaction equation

HRID 2251297 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N(CC)C(C)C)(C)C.[CH3:46][N:47]([CH3:63])[CH:48]1[CH2:52][CH2:51][N:50]([C:53]2[CH:62]=[CH:61][C:56]([C:57]([NH:59][NH2:60])=[O:58])=[CH:55][CH:54]=2)[CH2:49]1>O.CN(C=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:60][NH:59][C:57](=[O:58])[C:56]2[CH:55]=[CH:54][C:53]([N:50]3[CH2:51][CH2:52][CH:48]([N:47]([CH3:46])[CH3:63])[CH2:49]3)=[CH:62][CH:61]=2)=[O:12])=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 729714-Butoxybenzoic acidHCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 692131084-(3-Dimethylaminopyrrolidin-1-yl)benzohydrazide

Product 1

HCID 69208757N'-(4-butoxybenzoyl)-4-(3-dimethylaminopyrrolidin-1-yl)benzohydrazide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-butoxybenzoic acid (156 mg) and DMF (10 ml) was mixed with TOTU (264 mg) and N,N-diisopropylethylamine (104 mg). After 10 minutes, 4-(3-dimethylaminopyrrolidin-1-yl)benzohydrazide (200 mg) was added. After one hour, the mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The product with the molecular weight of 424.55 (C24H32N4O3) was obtained in this way; MS (ESI): 425 (M+H+).

Workup

  1. waitAfter one hour
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product with the molecular weight of 424.55 (C24H32N4O3) was obtained in this way

Sources & evidence

ORD record
ord-90a1953210df42a280c8aad24f8dcf72
Source dataset
uspto-grants-2008_01
Patent number
US07319108B2

Linked notes

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