Ethyl Acetate → HCID 10386017, compound

HRID 2054469Notes

Reaction equation

HRID 2054469 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH:4]=O.[NH2:18][C:19]1[CH:20]=[C:21]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:22]=[CH:23][C:24]=1[NH2:25].OS([O-])=O.[Na+].CCOC(C)=O>CC(N(C)C)=O>[NH2:1][C:2]1[C:3]([C:4]2[NH:18][C:19]3[CH:20]=[C:21]([S:26]([NH2:29])(=[O:27])=[O:28])[CH:22]=[CH:23][C:24]=3[N:25]=2)=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:8][N:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 27359273,4-diaminobenzenesulfonamideHCID 23665763Sodium BisulfiteHCID 58668623HCID 58668623, compound

Product 1

HCID 10386017HCID 10386017, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
200 °C

Procedure

2-amino-5-(4-methoxyphenyl)nicotinaldehyde (61.6 mg, 0.27 mmol), 3,4-diaminobenzene-1-sulphonamide (59.7 mg, 0.32 mmol), and NaHSO3 (29.2 mg, 0.4 mmol) were suspended in 3 ml dimethylacetamide. The reaction mixture was heated to 200° C. for 10 min in the SmithSynthesizer™ microwave instrument. Upon cooling, 5 ml of 4:1H2O/EtOAc was added to afford a slurry which was stirred for 1 h. The solids were collected via vacuum filtration, washed with water and then diethyl ether, and dried under vacuum for 15 hours to yield 2-[2-amino-5-(4-methoxyphenyl)pyridin-3-yl]-1H-benzimidazole-6-sulfonamide (16 mg).

Workup

  1. temperatureUpon cooling
  2. customto afford a slurry which
  3. filtrationThe solids were collected via vacuum filtration
  4. washwashed with water
  5. dry with materialdiethyl ether, and dried under vacuum for 15 hours

Sources & evidence

ORD record
ord-2fd12dcc16904de5948a5101db4c43f5
Source dataset
uspto-grants-2008_02
Patent number
US07329678B2

Reaction notes

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