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 1747415Notes

Reaction equation

HRID 1747415 reaction equation
[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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 76096Phenylsulphonyl isocyanate2×HCID 594974891-(2-Amino-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-6c9008f7e214450f9d232ba9a9810e22
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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