Hydrochloric Acid → N-{(S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoyl}-benzenesulfonamide

HRID 1747416Notes

Reaction equation

HRID 1747416 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]([C@@H:22]([CH2:27][CH2:28][CH3:29])[CH2:23][C:24]([OH:26])=O)[C:14]2=[O:30])=[CH:3]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[C:43]1([S:49]([NH2:52])(=[O:51])=[O:50])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C1CCN2C(=NCCC2)CC1.Cl>O.C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]([C@@H:22]([CH2:27][CH2:28][CH3:29])[CH2:23][C:24]([NH:52][S:49]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)(=[O:51])=[O:50])=[O:26])[C:14]2=[O:30])=[CH:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7370BenzenesulfonamideHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 25127851(S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid

Product 1

HCID 25126551N-{(S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoyl}-benzenesulfonamideYield 47.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

(S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid (25 mg, 0.062 mmol) is dissolved THF (0.5 mL) and CDI (22 mg, 0.14 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 (19 mg, 0.12 mmol) is added and after 10 min, DBU (0.018 mL, 0.12 mmol) is added. The mixture is then stirred for 16 hr at room temperature. 1 mL of 1.0 M HCl is added followed by 10 mL of water. The mixture is extracted with EtOAc (3×20 mL) and the organic layers are combined, dried and concentrated to give crude product. Purification by Preparative TLC affords 16 mg (47%) of N-{(S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoyl}-benzenesulfonamide. LCMS (ESMS): m/z 545.32 (M+H+).

Workup

  1. additionis added into it at room temperature
  2. temperatureAfter the mixture is cooled down to room temperature
  3. stirringThe mixture is then stirred for 16 hr at room temperature
  4. extractionThe mixture is extracted with EtOAc (3×20 mL)
  5. customdried
  6. concentrationconcentrated
  7. customto give crude product
  8. customPurification by Preparative TLC

Sources & evidence

ORD record
ord-f07bef8881fb48eeafdf407f1af0c02b
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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