Hydrochloric Acid → N-{3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionyl}-benzenesulfonamide

HRID 1747325Notes

Reaction equation

HRID 1747325 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[N:14]([CH2:21][CH2:22][C:23](O)=[O:24])[C:13]3=[O:26])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:39]1([S:45]([NH2:48])(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.N12CCCN=C1CCCCC2.Cl>C1COCC1.O>[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[N:14]([CH2:21][CH2:22][C:23]([NH:48][S:45]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)(=[O:47])=[O:46])=[O:24])[C:13]3=[O:26])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7370BenzenesulfonamideHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 566667203-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid

Product 1

HCID 25123879N-{3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionyl}-benzenesulfonamideYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid (150 mg, 0.41 mmol) is dissolved in dry THF (3.0 mL) and 1,1′-carbonyl diimidazole (150 mg, 0.92 mmol) is added into it at room temperature. The mixture is stirred for 30 min and then it is heated at 55° C. for 1 hr. After the mixture is cooled down to room temperature, benzenesulfonamide (130 mg, 0.82 mmol) is added and after 10 min, 1,8-diazabicyclo[5,4,0]undec-7-ene (0.12 mL, 0.82 mmol) is added. The mixture is stirred for 5 hr at room temperature and then 1.0 M HCl (3 mL) is added followed by water (30 mL). The mixture is extracted with EtOAc (3×50 mL) and the organic layers are combined, dried and concentrated to give crude product. Purification by preparative TLC using 75% EtOAc in Hexanes affords 123 mg (60%) of N-{3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionyl}-benzenesulfonamide. LCMS (ESMS): m/z 506.18 (M+H+).

Workup

  1. temperatureAfter the mixture is cooled down to room temperature
  2. stirringThe mixture is stirred for 5 hr at room temperature
  3. extractionThe mixture is extracted with EtOAc (3×50 mL)
  4. customdried
  5. concentrationconcentrated
  6. customto give crude product
  7. customPurification by preparative TLC

Sources & evidence

ORD record
ord-8d22deba07aa4f9db710f0c74fad2ae0
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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