Diisopropylethylamine → 3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid N'-(2-ethyl-6-methyl-pyridine-4-carbonyl)-hydrazide

HRID 2366130Notes

Reaction equation

HRID 2366130 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=O)=[C:5]2[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH2:14][C:4]=12)[CH3:2].Cl.[CH2:18]([C:20]1[CH:21]=[C:22]([CH:27]=[C:28]([CH3:30])[N:29]=1)[C:23]([NH:25][NH2:26])=[O:24])[CH3:19].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CCOCC>[CH2:18]([C:20]1[CH:21]=[C:22]([C:23]([NH:25][NH:26][C:8]([C:6]2[S:7][C:3]([CH2:1][CH3:2])=[C:4]3[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][C:5]=23)=[O:10])=[O:24])[CH:27]=[C:28]([CH3:30])[N:29]=1)[CH3:19]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 574374183-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acidHCID 675203072-Ethyl-6-methyl-isonicotinic acid hydrazide hydrochloride

Product 1

HCID 675204483-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid N'-(2-ethyl-6-methyl-pyridine-4-carbonyl)-hydrazide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (114 mg, 0.48 mmol), 2-ethyl-6-methyl-isonicotinic acid hydrazide hydrochloride (120.5 mg, 0.48 mmol) and DIPEA (0.49 mL) in DMF (8 mL) is added TBTU (190 mg, 0.59 mmol). The mixture is stirred at rt for 15 h. The mixture is diluted with Et2O (50 mL) and extracted with 1M aq. NaOH (2×20 mL). The aq. extracts are washed with EA (2×20 mL) and the combined organic phases are dried (MgSO4), filtered and evaporated to give crude 3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid N′-(2-ethyl-6-methyl-pyridine-4-carbonyl)-hydrazide; LC-MS: tR=0.83 min, [M+1]=400.31.

Workup

  1. extractionextracted with 1M aq. NaOH (2×20 mL)
  2. washThe aq. extracts are washed with EA (2×20 mL)
  3. dry with materialthe combined organic phases are dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-fd8e8a7197fa45b0b8809bebe127062e
Source dataset
uspto-grants-2014_04
Patent number
US08697732B2

Reaction notes

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