Triethylamine → 4-allyloxy-3,5-dimethyl-benzoic acid N'-(4-isobutyl-3-methyl-thiophene-2-carbonyl)-hydrazide

HRID 1676141Notes

Reaction equation

HRID 1676141 reaction equation
[CH2:1]([C:5]1[C:6]([CH3:13])=[C:7]([C:10]([OH:12])=O)[S:8][CH:9]=1)[CH:2]([CH3:4])[CH3:3].Cl.[CH2:15]([O:18][C:19]1[C:28]([CH3:29])=[CH:27][C:22]([C:23]([NH:25][NH2:26])=[O:24])=[CH:21][C:20]=1[CH3:30])[CH:16]=[CH2:17].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.C(OCC)C>[CH2:1]([C:5]1[C:6]([CH3:13])=[C:7]([C:10]([NH:26][NH:25][C:23](=[O:24])[C:22]2[CH:21]=[C:20]([CH3:30])[C:19]([O:18][CH2:15][CH:16]=[CH2:17])=[C:28]([CH3:29])[CH:27]=2)=[O:12])[S:8][CH:9]=1)[CH:2]([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 594978694-Isobutyl-3-methylthiophene-2-carboxylic acidHCID 673521894-Allyloxy-3,5-dimethylbenzoic acid hydrazide hydrochloride

Product 1

HCID 673514084-allyloxy-3,5-dimethyl-benzoic acid N'-(4-isobutyl-3-methyl-thiophene-2-carbonyl)-hydrazideYield 79.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-isobutyl-3-methyl-thiophene-2-carboxylic acid (100 mg, 0.5 mmol), 4-allyloxy-3,5-dimethyl-benzoic acid hydrazide hydrochloride (192 mg, 0.75 mmol) and NEt3 (0.28 mL) in DMF (10 mL) is cooled at 0° C. and TBTU (200 mg, 0.6 mmol) is added. The mixture is stirred for 15 h while warming from 0° C. to rt. The mixture is diluted with diethyl ether (50 mL) and washed with 1M aq. NaOH (2×20 mL), 1M aq. HCl (2×20 mL) and brine (10 mL). The organic phase is dried (Na2SO4), filtered and evaporated to give 160 mg of 4-allyloxy-3,5-dimethyl-benzoic acid N′-(4-isobutyl-3-methyl-thiophene-2-carbonyl)-hydrazide; LC-MS: tR=1.05 min, [M+1]+=400.83.

Workup

  1. temperaturewhile warming from 0° C. to rt
  2. washwashed with 1M aq. NaOH (2×20 mL), 1M aq. HCl (2×20 mL) and brine (10 mL)
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3a169375ada1494eaeb59467cf2cb4ba
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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