Ammonium Chloride → HCID 68772647, compound

HRID 1628419Notes

Reaction equation

HRID 1628419 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[CH:13]=[N:14][C:15]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:16][C:17]=3[CH3:18])[N:7]([CH2:24][CH2:25][CH2:26][C:27](OCC)=[O:28])[C:6]=2[C:5]([CH:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:4][CH:3]=1.[BH4-].[Li+].[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[CH:13]=[N:14][C:15]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:16][C:17]=3[CH3:18])[N:7]([CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[C:6]=2[C:5]([CH:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 68761864Ethyl 4-{4-chloro-7-(1-ethylpropyl)-2-[(4-methyl-6-pyrrolidin-1-ylpyridin-3-yl)amino]-1H-benzimidazol-1-yl}butanoate

Product 1

HCID 68772647HCID 68772647, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-{4-chloro-7-(1-ethylpropyl)-2-[(4-methyl-6-pyrrolidin-1-ylpyridin-3-yl)amino]-1H-benzimidazol-1-yl}butanoate (650 mg, 1.27 mmol) in tetrahydrofuran (5 mL) was added lithium borohydride (84 mg, 3.82 mmol) portionwise at 0° C. The mixture was warmed to room temperature and stirred for 24 hr. Aqueous ammonium chloride was added and the mixture was stirred for 30 minutes followed by addition of aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a light brown solid, which was recrystallized from ethyl acetate/isopropyl ether to give the title compound (375 mg, 0.798 mmol, 63%) as a colorless solid.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionThe mixture was extracted with ethyl acetate
  3. washOrganic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a light brown solid, which
  7. customwas recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-584c4dd01e964ade91afb43e16ff0123
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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