5-(N-t-butoxycarbonylindol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole → HCID 67497943, compound

HRID 74206Notes

Reaction equation

HRID 74206 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:32]=[CH:31][C:20]2[N:21]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:22]([CH3:24])=[N:23][C:19]=2[CH:18]=1)=O)(C)(C)C>Cl>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:32]=[CH:31][C:20]2[N:21]([CH:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[C:22]([CH3:24])=[N:23][C:19]=2[CH:18]=1

Participants

3

Reactant 1

HCID 674982575-(N-t-butoxycarbonylindol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole

Product 1

HCID 67497943HCID 67497943, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-(N-t-butoxycarbonylindol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole (see Synthesis Example 37 (200 mg, 0.463 mmol) was added to a 1N aqueous hydrochloric acid solution (10 mL), and this was stirred at room temperature for 3 hours. After the reaction was complete, this was allowed to stand for 3 days and the precipitated crystals were filtered off, and to this was added saturated aqueous sodium hydrogen carbonate (5 mL) and this was stirred for 30 minutes. The precipitated crystals were filtered off, washed with water and dried to yield the title compound (155 mg, quant.) as light brown crystals.

Workup

  1. waitto stand for 3 days
  2. filtrationthe precipitated crystals were filtered off
  3. additionto this was added saturated aqueous sodium hydrogen carbonate (5 mL)
  4. stirringthis was stirred for 30 minutes
  5. filtrationThe precipitated crystals were filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-1cd7e1f954d44114a1fde5ccb2fe9a68
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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