Dimethylformamide → HCID 57937599, compound

HRID 1435136Notes

Reaction equation

HRID 1435136 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][C:11]1[CH:12]=[C:13]([N:20]2[C:24]3[CH:25]=[CH:26][C:27]([C:29](O)=[O:30])=[CH:28][C:23]=3[N:22]=[CH:21]2)[S:14][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[CH3:9].C(N(C(C)C)CC)(C)C.[C:41]([NH:44][NH2:45])(=[O:43])[CH3:42].CN(C=O)C>C(Cl)Cl.O>[C:41]([NH:44][NH:45][C:29]([C:27]1[CH:26]=[CH:25][C:24]2[N:20]([C:13]3[S:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:11]([O:10][C@@H:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[CH3:9])[CH:12]=3)[CH:21]=[N:22][C:23]=2[CH:28]=1)=[O:30])(=[O:43])[CH3:42]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14039AcetohydrazideHCID 81531DiisopropylethylamineHCID 685699691-{4-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-[(methyloxy)carbonyl]-2-thienyl}-1H-benzimidazole-5-carboxylic acid2×

Product 1

HCID 57937599HCID 57937599, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A 20.0 mL flask was charged with 150 mg (0.329 mmol) of 1-{4-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-[(methyloxy)carbonyl]-2-thienyl}-1H-benzimidazole-5-carboxylic acid (Intermediate 34, 0.120 mL, 0.658 mmol) of diisopropyl ethylamine, 24.4 mg (0.329 mmol) of acethydrazide and 2.00 ml of DMF. Next, 125 mg (0.329 mmol) of O-(7-Aza benzotriazole-1-yl)-N,N,N′,N′ tetramethyluranium hexafluoro phosphate was added and the reaction mixture stirred at rt for 30 min. 10 mL of water and 30 mL of DCM was added and the organic layer separated. The organic layer was adsorbed onto silica gel and chromatographed to give 154 mg (91% yield) of a tan solid. MS (APCI): 513 [M+H]+.

Workup

  1. customthe organic layer separated
  2. customchromatographed

Sources & evidence

ORD record
ord-252524b17ac3428a9a2e177da461c5a4
Source dataset
uspto-grants-2009_11
Patent number
US07615643B2

Reaction notes

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