Hydrochloric Acid → HCID 59497267, compound

HRID 1747319Notes

Reaction equation

HRID 1747319 reaction equation
[C:1]1([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]([CH2:21][CH2:22][C:23](O)=[O:24])[C:13]2=[O:26])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=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>[C:1]1([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]([CH2:21][CH2:22][C:23]([NH:48][S:45]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)(=[O:47])=[O:46])=[O:24])[C:13]2=[O:26])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7370BenzenesulfonamideHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 56666721HCID 56666721, compound

Product 1

HCID 59497267HCID 59497267, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(3-Naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid (80 mg, 0.23 mmol) is dissolved in dry THF (3.0 mL) and 1,1′-carbonyl diimidazole (84 mg, 0.52 mmol) is added into it. The mixture is stirred for 30 min at room temperature and then it is heated at 55° C. for 1 hr. After the mixture is cooled down to room temperature, benzenesulfonamide (73 mg, 0.46 mmol) is added and after 10 min, 1,8-diazabicyclo[5,4,0]undec-7-ene (0.07 mL, 0.46 mmol) is added. The mixture is again stirred for 8 heat room temperature. 1.0 M HCl aqueous solution (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 55% EtOAc in Hexanes affords 66 mg (59%) of N-[3-(3-Naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionyl]-benzenesulfonamide. LCMS (ESMS): m/z 486.05 (M+H+)

Workup

  1. temperatureit is heated at 55° C. for 1 hr
  2. temperatureAfter the mixture is cooled down to room temperature
  3. stirringThe mixture is again stirred for 8
  4. temperatureheat room temperature
  5. extractionThe mixture is extracted with EtOAc (3×50 mL)
  6. customdried
  7. concentrationconcentrated
  8. customto give crude product
  9. customPurification by preparative TLC

Sources & evidence

ORD record
ord-3a4d0bf60ae949f6a723a977b90cbf90
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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