Hydrochloric Acid → N-[(2-{3-[(4-methyl-1-benzothien-3-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}ethyl)carbamoyl]benzenesulfonamide

HRID 1747415노트

반응식

HRID 1747415 반응식
[NH2:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[C:15]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:16]=3[S:17][CH:18]=2)[C:5]1=[O:24].C(N(CC)CC)C.[C:32]1([S:38]([N:41]=[C:42]=[O:43])(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl>O.C(Cl)Cl>[CH3:23][C:22]1[C:15]2[C:14]([CH2:13][N:6]3[C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[N:4]([CH2:3][CH2:2][NH:1][C:42]([NH:41][S:38]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)(=[O:40])=[O:39])=[O:43])[C:5]3=[O:24])=[CH:18][S:17][C:16]=2[CH:19]=[CH:20][CH:21]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 76096Phenylsulphonyl isocyanate2회HCID 594974891-(2-Amino-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

생성물 1

HCID 25124205N-[(2-{3-[(4-methyl-1-benzothien-3-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}ethyl)carbamoyl]benzenesulfonamide수율 76.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

1-(2-Amino-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (28 mg, 0.083 mmol) is added into DCM (1.0 mL) at room temperature and triethylamine (0.014 mL, 0.10 mmol) is added. Then Benzenesulfonyl isocyanate (0.014 mL, 0.10 mmol) is added into the above reaction mixture. After stirring for 2 hr, another 0.014 mL of Benzenesulfonyl isocyanate is added and the mixture is further stirred for 30 min. Then 1.0 mL of 1.0M HCl is added along with 5 mL of water. The mixture is extracted with EtOAc (3×20 mL) and the organic layers are combined, dried (Na2SO4) and concentrated to give crude product. Purification by preparative TLC affords 33 mg (76%) of the title compound. LCMS (ESMS): m/z 521.17 (M+H+).

후처리

  1. stirringthe mixture is further stirred for 30 min
  2. extractionThe mixture is extracted with EtOAc (3×20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give crude product
  6. customPurification by preparative TLC

출처 및 근거

ORD 기록
ord-6c9008f7e214450f9d232ba9a9810e22
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150556B2

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