Thiophene-2-carbohydrazide → thiophene-2-carboxylic acid N'-[4-(3-chloro-phenyl)-2-(5,6-dimethoxy benzoimidazol-1-yl)-thiazole-5-carbonyl]-hydrazide

HRID 1785520Notes

Reaction equation

HRID 1785520 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:16]3[C:20]4[CH:21]=[C:22]([O:27][CH3:28])[C:23]([O:25][CH3:26])=[CH:24][C:19]=4[N:18]=[CH:17]3)[S:11][C:12]=2[C:13]([OH:15])=O)[CH:5]=[CH:6][CH:7]=1.[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([NH:36][NH2:37])=[O:35].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:16]3[C:20]4[CH:21]=[C:22]([O:27][CH3:28])[C:23]([O:25][CH3:26])=[CH:24][C:19]=4[N:18]=[CH:17]3)[S:11][C:12]=2[C:13]([NH:37][NH:36][C:34]([C:30]2[S:29][CH:33]=[CH:32][CH:31]=2)=[O:35])=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 73098Thiophene-2-carbohydrazideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 236540194-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid

Product 1

HCID 57595850thiophene-2-carboxylic acid N'-[4-(3-chloro-phenyl)-2-(5,6-dimethoxy benzoimidazol-1-yl)-thiazole-5-carbonyl]-hydrazideYield 70.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (41 mg, 0.1 mmol) and thiophene-2-carboxylic acid hydrazide (14.2 mg, 0.1 mmol, Aldrich) in N,N-dimethylformamide (1 ml) was added HATU (38 mg, 0.1 mmol) and diisopropylethylamine (26 μl, 0.15 mmol). The mixture was stirred at ambient temperature overnight. The solvent was reduced in vacuo and water (3 ml) was added. After sonication, the crude was filtered and sent directly for purification with prep-HPLC to afford thiophene-2-carboxylic acid N′-[4-(3-chloro-phenyl)-2-(5,6-dimethoxy benzoimidazol-1-yl)-thiazole-5-carbonyl]-hydrazide (37.9 mg, 70.2%) as a white solid. MS m/z 540 (M+1).

Workup

  1. additionwas added
  2. customAfter sonication
  3. filtrationthe crude was filtered
  4. customsent directly for purification with prep-HPLC

Sources & evidence

ORD record
ord-79c97d7eb5cf42ed9c08b38a0ff2f9fc
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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