Acetic Acid → HCID 68762386, compound

HRID 1628464Notes

Reaction equation

HRID 1628464 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([CH2:22][CH2:23][CH2:24][OH:25])[C:9]([NH:11][C:12]3[C:13]([O:20][CH3:21])=[N:14][C:15]([O:18][CH3:19])=[N:16][CH:17]=3)=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:26](=O)[CH3:27].[C:29](O)(=O)[CH3:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:29]([N:1]([CH2:26][CH3:27])[C:2]1[C:7]2[N:8]([CH2:22][CH2:23][CH2:24][OH:25])[C:9]([NH:11][C:12]3[C:13]([O:20][CH3:21])=[N:14][C:15]([O:18][CH3:19])=[N:16][CH:17]=3)=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:30]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68766787HCID 68766787, compound

Product 1

HCID 68762386HCID 68762386, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-{7-amino-2-[(2,4-dimethoxypyrimidin-5-yl)amino]-1H-benzimidazol-1-yl}propan-1-ol (99 mg, 0.287 mmol), acetaldehyde (90%, 0.178 mL, 2.87 mmol) and acetic acid (0.066 mL, 1.15 mmol) in tetrahydrofuran (2.0 mL) was added sodium triacetoxyborohydride (384 mg, 1.72 mmol) portionwise at 0° C. The mixture was warmed to room temperature and stirred for 14 hr. Aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 5.0-100% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound (90 mg, 0.224 mmol, 78%) as a colorless amorphous.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washOrganic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with a 5.0-100% ethyl acetate/n-hexane gradient mixture
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-10a34230d3c748b1ba78f61af1b6f2b1
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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