Hydrochloric Acid → HCID 89702209, compound

HRID 2202968Notes

Reaction equation

HRID 2202968 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]4[N:21]=[C:20]([CH:22]5[CH2:24][CH:23]5[C:25](OC)=[O:26])[N:19]([CH3:29])[C:18]=4[CH:30]=3)[C:10](=[O:31])[CH:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[Cl-].[Ca+2].Cl>C1COCC1.CO>[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]4[N:21]=[C:20]([CH:22]5[CH2:24][CH:23]5[CH2:25][OH:26])[N:19]([CH3:29])[C:18]=4[CH:30]=3)[C:10](=[O:31])[CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride2×HCID 5284359Calcium ChlorideHCID 121386252HCID 121386252, compound

Product 1

HCID 89702209HCID 89702209, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of methyl(1RS,2SR)-2-(6-(4-((4-chlorobenzyl)oxy)-2-oxopyridin-1(2H)-yl)-1-methyl-1H-benzimidazol-2-yl)cyclopropanecarboxylate (200 mg) in THF (1.5 ml) and MeOH (0.750 ml) was added dropwise to a solution of NaBH4 (32.6 mg) and CaCl2 (71.8 mg) in THF (3 ml) and MeOH (2 ml) at 0° C. The mixture was stirred at room temperature under Ar atmosphere overnight. NaBH4 (300 mg) was added to the m resulting mixture at 50° C., and the mixture was stirred at 50° C. overnight. The mixture was neutralized with 1 M HCl at 0° C. and extracted with EtOAc. The organic layer was separated, washed with saturated NaHCO3 solution and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (156 mg) as a white solid.

Workup

  1. customresulting mixture at 50° C.
  2. stirringthe mixture was stirred at 50° C. overnight
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with saturated NaHCO3 solution and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-2e0306aa54f0436e9cbefc801482a9ee
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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