Hydrochloric Acid → HCID 11005397, compound

HRID 1072933Notes

Reaction equation

HRID 1072933 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][C:6]1[C:7]2[CH:15]=[C:14]([C:16](O)=[O:17])[CH:13]=[CH:12][C:8]=2[S:9][C:10]=1[CH3:11].C(C1NC=CN=1)(C1NC=CN=1)=O.[CH2:35]([S:40]([NH2:43])(=[O:42])=[O:41])[CH2:36][CH2:37][CH2:38][CH3:39].N12CCCN=C1CCCCC2.Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][C:6]1[C:7]2[CH:15]=[C:14]([C:16](=[O:17])[NH:43][S:40]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])(=[O:42])=[O:41])[CH:13]=[CH:12][C:8]=2[S:9][C:10]=1[CH3:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 109206961-PentanesulfonamideHCID 11100229HCID 11100229, compound

Product 1

HCID 11005397HCID 11005397, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3,4-Dichlorobenzyl)-2-methylbenzo[b]thiophene-5-carboxylic acid (160 mg) was dissolved in dry dimethylformamide (2 ml). Carbonyl-diimidazole (111 mg) was added and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were added n-pentanesulfonamide (108 mg) and 1,8-diazabicyclo[5,4,0]undec-7-ene (122 mg) and the mixture was stirred at 100° C. for 1.5 hr. The reaction mixture was cooled in ice, and the pH thereof was adjusted to pH 4 with 1N hydrochloric acid. The mixture was partitioned between ethyl acetate and water. The organic layer was washed twice with water, dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was eluted by silica gel column chromatography (hexane:ethyl acetate=1:1). The resulting residue was crystallized from hexane-ethyl acetate to give 3-(3,4-dichlorobenzyl)-2-methyl-5-(n-pentanesulfonyl-carbamoyl)benzo[b]thiophene (118 mg).

Workup

  1. stirringthe mixture was stirred at 100° C. for 1.5 hr
  2. temperatureThe reaction mixture was cooled in ice
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed twice with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure
  7. washThe residue was eluted by silica gel column chromatography (hexane:ethyl acetate=1:1)
  8. customThe resulting residue was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-9f44a567b86845a6b790fcbead96f22b
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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