Hydrochloric Acid → HCID 11005397, 화합물

HRID 1699953노트

반응식

HRID 1699953 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

HCID 11005397HCID 11005397, 화합물수율 53.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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-pentanesulfonylcarbamoyl)benzo[b]thiophene (118 mg).

후처리

  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

출처 및 근거

ORD 기록
ord-7f625d11673a4f00a6847b4ed5f34dba
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06348474B1

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