Water → HCID 68869725, compound

HRID 1817863Notes

Reaction equation

HRID 1817863 reaction equation
[H-].[Na+].[CH3:3][CH:4]([SH:6])[CH3:5].Cl[CH2:8][C:9]1[CH:26]=[CH:25][C:12]2[N:13]([CH2:21][CH:22]3[CH2:24][CH2:23]3)[C:14]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:15][C:11]=2[CH:10]=1.O>CN(C)C=O>[CH:22]1([CH2:21][N:13]2[C:12]3[CH:25]=[CH:26][C:9]([CH2:8][S:6][CH:4]([CH3:5])[CH3:3])=[CH:10][C:11]=3[N:15]=[C:14]2[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 63642-PropanethiolHCID 24758Sodium hydrideHCID 68869754HCID 68869754, compound

Product 1

HCID 68869725HCID 68869725, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (washed with hexane, 30 mg, 1.3 mmol) in N,N-dimethylformamide (2 mL) was added 2-propanethiol (117 μL, 1.3 mmol) at 0° C. After stirring for 30 min, a N,N-dimethylformamide solution of 5-(chloromethyl)-1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazole (Step E) was added and the mixture was stirred at 100° C. for 17.5 h. Water (5 mL) was added and the mixture was extracted with ethyl acetate (15 mL×2) and washed with brine (5 mL). The organic extracts were dried over sodium sulfate and concentrated. The residue was purified by pTLC (hexane:ethyl acetate=3:1) to give the title compound (74 mg, 67% over 2 steps) as pale brown oil.

Workup

  1. stirringthe mixture was stirred at 100° C. for 17.5 h
  2. extractionthe mixture was extracted with ethyl acetate (15 mL×2)
  3. washwashed with brine (5 mL)
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by pTLC (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-936c5f0a307a4a7889e97c00030b7cf1
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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