Ammonium Chloride → 1-{[1-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methyl}azetidin-3-ol

HRID 1628675

Reaction equation

HRID 1628675 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2=[N:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([N:24]4[CH2:27][CH:26]([OH:28])[CH2:25]4)=O)[C:17]=3[N:13]2[CH2:12][CH2:11][CH2:10]1.[B].O1CCCC1.[Cl-].[NH4+]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2=[N:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:24]4[CH2:27][CH:26]([OH:28])[CH2:25]4)[C:17]=3[N:13]2[CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 11062302Borane-tetrahydrofuranHCID 577860241-{[1-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]carbonyl}azetidin-3-ol

Product 1

HCID 577858111-{[1-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methyl}azetidin-3-olYield 63.2%

Conditions

Temperature
70 °C

Procedure

To a suspension of 1-{[1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]carbonyl}azetidin-3-ol (150 mg, 0.359 mmol) was added boron-tetrahydrofuran complex (1.0 M solution in tetrahydrofuran, 1.8 mL, 1.8 mmol), and the mixture was stirred at 70° C. for 13 hr. To the mixture was added aqueous saturated ammonium chloride, and the mixture was stirred at 70° C. for 20 min. The mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the solid, which was washed with ethanol to give the title compound as a colorless powder (91.5 mg, 0.227 mmol, 63%).

Workup

  1. stirringthe mixture was stirred at 70° C. for 20 min
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the solid, which
  8. washwas washed with ethanol

Sources & evidence

ORD record
ord-27e65e1702cb4679b55113cf36e13315
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Linked notes

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