Hydrochloric Acid → 2-(1,2,3,4-Tetrahydroquinolin-2-yl)-1H-benzo[d]imidazole-4-carboxamide

HRID 1895551Notes

Reaction equation

HRID 1895551 reaction equation
[C:1]([C:4]1[C:12]2[N:11]=[C:10]([CH:13]3[CH2:22][CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]3C(OC(C)(C)C)=O)[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[NH2:2].Cl>CO>[NH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:21][CH2:22][CH:13]1[C:10]1[NH:9][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 49854327tert-butyl 2-(4-carbamoyl-1H-benzo[d]imidazol-2-yl)-3,4-dihydroquinoline-1(2H)-carboxylate

Product 1

HCID 498543282-(1,2,3,4-Tetrahydroquinolin-2-yl)-1H-benzo[d]imidazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of tert-butyl 2-(4-carbamoyl-1H-benzo[d]imidazol-2-yl)-3,4-dihydroquinoline-1(2H)-carboxylate (17 mg, 0.043 mmol) and HCl in methanol (1.25 M, 1 mL) was stirred at 40° C. overnight. Methanol was removed under reduced pressure, aq. sodium bicarbonate solution was added and extracted with DCM. The DCM layer was washed with brine, dried over anhydrous sodium sulfate and evaporated to afford 2-(1,2,3,4-Tetrahydroquinolin-2-yl)-1H-benzo[d]imidazole-4-carboxamide. MS (ES+): m/z 315.13 [M+Na]+

Workup

  1. customMethanol was removed under reduced pressure, aq. sodium bicarbonate solution
  2. additionwas added
  3. extractionextracted with DCM
  4. washThe DCM layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-70c441dace72432b8d8c5908e38add49
Source dataset
uspto-grants-2013_08
Patent number
US08513433B2

Reaction notes

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