Diisopropylethylamine → 6-isobutyl-5-methyl-nicotinic acid N'-(4-allyloxy-3,5-dimethyl-benzoyl)-hydrazide

HRID 2065918Notes

Reaction equation

HRID 2065918 reaction equation
Cl.[CH2:2]([C:6]1[C:14]([CH3:15])=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][N:7]=1)[CH:3]([CH3:5])[CH3:4].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:47]([O:50][C:51]1[C:60]([CH3:61])=[CH:59][C:54]([C:55]([NH:57][NH2:58])=[O:56])=[CH:53][C:52]=1[CH3:62])[CH:48]=[CH2:49]>C(Cl)Cl.CC(=O)OCC>[CH2:47]([O:50][C:51]1[C:60]([CH3:61])=[CH:59][C:54]([C:55]([NH:57][NH:58][C:10](=[O:12])[C:9]2[CH:13]=[C:14]([CH3:15])[C:6]([CH2:2][CH:3]([CH3:4])[CH3:5])=[N:7][CH:8]=2)=[O:56])=[CH:53][C:52]=1[CH3:62])[CH:48]=[CH2:49]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 592020394-Allyloxy-3,5-dimethyl-benzoic acid hydrazideHCID 670271826-Isobutyl-5-methyl-nicotinic acid hydrochloride

Product 1

HCID 687652896-isobutyl-5-methyl-nicotinic acid N'-(4-allyloxy-3,5-dimethyl-benzoyl)-hydrazideYield 97.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-isobutyl-5-methyl-nicotinic acid hydrochloride (50 mg, 0.22 mmol), DIPEA (0.12 mL, 0.7 mmol) and TBTU (97 mg, 0.30 mmol) in DCM (5 mL) is added at 0° C. 4-allyloxy-3,5-dimethyl-benzoic acid hydrazide (50.6 mg, 0.23 mmol) and the mixture is stirred at 0° C. for 4 h. The mixture is diluted with EA (15 mL) and washed with 1M aq. NaH2PO4 (5 mL), 1M aq. NaOH (5 mL) and water (5 mL). The org. phase is dried (MgSO4), filtered and evaporated to provide 6-isobutyl-5-methyl-nicotinic acid N′-(4-allyloxy-3,5-dimethyl-benzoyl)-hydrazide (85 mg); LC-MS: tR=0.81 min, [M+1]+=396.20.

Workup

  1. washwashed with 1M aq. NaH2PO4 (5 mL), 1M aq. NaOH (5 mL) and water (5 mL)
  2. dry with materialphase is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-523c4908a0b248f2a27898e77dab6b7c
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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