Acetic Acid → HCID 67539132, compound

HRID 2240949Notes

Reaction equation

HRID 2240949 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=2)([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[CH:11][CH:10]=2)[N:3]=1.[CH:26](=O)[CH2:27][CH3:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[Cl:48]C(Cl)C>C(Cl)Cl>[ClH:48].[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:17])[F:18])=[CH:11][CH:10]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][CH2:26][CH2:27][CH3:28])[CH:20]=2)[N:3]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 527PropanalHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 25123323HCID 25123323, compound

Product 1

HCID 67539132HCID 67539132, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture 2-amino-5-(3-amino-phenyl)-5-(4-difluoromethoxy-phenyl)-3-methyl-3,5-dihydro-imidazol-4-one (150 mg, 0.43 mmol), propionaldehyde (25 mg, 0.43 mmol), sodium triacetoxyborohydride (184 mg, 0.87 mmol), and acetic acid (0.87 mmol) in dichloroethane (4.3 mL) was stirred at room temperature overnight. The reaction was diluted with methylene chloride and washed with sodium carbonate. The organic layer was concentrated and purified by reverse-phase HPLC followed by treatment with hydrochloric acid to provide the title compound (122 mg, 73%), characterized by NMR and mass spectral analyses. MS (ES+) m/e 389 (M+H)+.

Workup

  1. washwashed with sodium carbonate
  2. concentrationThe organic layer was concentrated
  3. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-30f022f62ba647fb8f98172e53d8e866
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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