Benzoic Acid → HCID 25124529, compound

HRID 1747344Notes

Reaction equation

HRID 1747344 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:22][C:23]1[C:31]2[C:30]([CH2:32][N:33]3[C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=4[N:35]([CH2:42][CH2:43][S:44]([NH2:47])(=[O:46])=[O:45])[C:34]3=[O:48])=[CH:29][S:28][C:27]=2[CH:26]=[CH:25][CH:24]=1.N12CCCN=C1CCCCC2.Cl>O.C1COCC1>[C:1]([NH:47][S:44]([CH2:43][CH2:42][N:35]1[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[N:33]([CH2:32][C:30]2[C:31]3[C:23]([CH3:22])=[CH:24][CH:25]=[CH:26][C:27]=3[S:28][CH:29]=2)[C:34]1=[O:48])(=[O:46])=[O:45])(=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 243Benzoic AcidHCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59497515HCID 59497515, compound

Product 1

HCID 25124529HCID 25124529, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

Benzoic acid (6.1 mg, 0.050 mmol) is dissolved THF (0.50 mL) and 1,1′-carbonyl diimidazole (9.1 mg, 0.056 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, 2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid amide (10 mg, 0.025 mmol) is added and after 10 min, 1,8-diazabicyclo[5,4,0]undec-7-ene (0.007 mL, 0.050 mmol) is added. The mixture is stirred for 16 hr at room temperature. 1.0 M HCl solution (1.0 mL) is added followed by water (10 mL). 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 using 6% MeOH in EtOAc affords 11 mg (85%) of 2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid benzoylamide. LCMS (ESMS): m/z 506.25 (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 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-87ad4489f38149d182fbba20d64ea6a5
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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