Hydrochloric Acid → HCID 86745540, compound

HRID 1728561Notes

Reaction equation

HRID 1728561 reaction equation
C([N:9]1[CH2:18][CH2:17][C:16]2[NH:15][C:14](=[O:19])[N:13]3[CH:20]=[C:21](C4C=CC=CC=4F)[N:22]=[C:12]3[C:11]=2[CH2:10]1)(=O)C1C=CC=NC=1.B.Cl.[OH-].[Na+]>C1COCC1.C(Cl)Cl>[N:22]1[CH:21]=[CH:20][N:13]2[C:12]=1[C:11]1[CH2:10][NH:9][CH2:18][CH2:17][C:16]=1[NH:15][C:14]2=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14798Sodium HydroxideHCID 10872814HCID 10872814, compound

Product 1

HCID 86745540HCID 86745540, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 9-(Nicotinoyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one (128 mg, 0.33 mmol), methylene chloride (3 mL) and 1M borane in THF (3.3 mL) was stirred at room temperature for 16 h. The reaction mixture was carefully acidified with 5 mL of 6N HCl and heated at reflux for 15 min. The reaction mixture was made alkaline with 10% NaOH and the product was extracted with 10% methanol in ethyl acetate. After drying over magnesium sulfate the solvent was removed in vacuo to afford a yellow solid which was recrystallized from ethanol to afford 9-(3-Pyridylmethyl)-2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e]pyrimidin-5(6H)-one (Compound 52) as a pale yellow solid, m.p. 290°-292° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 15 min
  3. extractionthe product was extracted with 10% methanol in ethyl acetate
  4. dry with materialAfter drying over magnesium sulfate the solvent
  5. customwas removed in vacuo
  6. customto afford a yellow solid which
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-e136c113ada141eabc3e56c8749af52e
Source dataset
uspto-grants-1994_07
Patent number
US05328912

Reaction notes

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