Triethylamine → HCID 57786341, compound

HRID 1399113Notes

Reaction equation

HRID 1399113 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:30])=[C:13]2[C:17]=1[N:16]=[C:15]1[N:18]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])[CH2:19][CH2:20][CH2:21][N:14]21.C(N(CC)CC)C.CC(C)([O-])C.[K+]>O1CCCC1.CO>[Cl:8][C:9]1[C:17]2[N:16]=[C:15]3[N:18]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=4[Cl:29])[CH2:19][CH2:20][CH2:21][N:14]3[C:13]=2[C:12]([N:30]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 23665647Potassium tert-butoxideHCID 577863289-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine

Product 1

HCID 57786341HCID 57786341, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Chlorobutanoyl chloride (88.2 mg, 0.626 mmol) was added to a stirred solution of 9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine (Example 100, 230 mg, 0.626 mmol) and triethylamine (0.18 mL) in tetrahydrofuran (6.0 ml) at 0° C., and the mixture was stirred at 0° C. for 2 hr. Methanol (1.0 mL) and potassium t-butoxide (351 mg, 3.13 mmol) were added to the mixture, and the mixture was stirred at 60° C. for 16 hr. The mixture was concentrated in vacuo, diluted with water, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 80-100% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/diisopropyl ether to give the title compound as a colorless crystal (85.8 mg, 0.197 mmol, 31%).

Workup

  1. stirringthe mixture was stirred at 60° C. for 16 hr
  2. concentrationThe mixture was concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel eluting with a 80-100% ethyl acetate/n-hexane gradient mixture
  10. concentrationThe filtrate was concentrated in vacuo
  11. customto give the solid, which
  12. customwas recrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-3e108ae93e9c4595965c9ac14e614897
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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