Acetic Acid → HCID 68416868, compound

HRID 2098584Notes

Reaction equation

HRID 2098584 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:9]([NH:11][CH:12]2[CH2:14][CH2:13]2)=[O:10])=[CH:4][CH:3]=1.[CH3:23][O:24][C:25](=[O:34])[C:26]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C.C(OCC)(=O)C.O>[CH:12]1([NH:11][C:9](=[O:10])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][CH2:32][C:29]3[CH:30]=[CH:31][C:26]([C:25]([O:24][CH3:23])=[O:34])=[CH:27][CH:28]=3)=[CH:3][CH:4]=2)=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 15294Methyl 4-FormylbenzoateHCID 5049666Sodium triacetoxyborohydrideHCID 68408134HCID 68408134, compound

Product 1

HCID 68416868HCID 68416868, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
37 °C

Procedure

To a solution of 2-(4-aminophenyl)-N-cyclopropyl-3-(4-fluorophenyl)acrylamide (0.34 g, 1.15 mmol, prepared according to the procedure described in Example 165, step-I) in dichloroethane (25 mL), methyl-4-formylbenzoate (0.185 g, 1.15 mmol) was added under stirring at 37° C. After stirring for 5 minutes, sodium triacetoxy borohydride (0.39 g, 1.85 mmol) was added to reaction mixture followed by acetic acid (0.3 mL). The reaction mixture was stirred for 8 hours at room temperature. Subsequently the reaction mixture was treated with ethyl acetate:water (1:1, 100 mL) and extracted with ethyl acetate (3×50 mL). The organic layer was washed with brine (100 mL) and dried over anhydrous sodium sulphate and evaporation afforded the title compound (0.42 g. 80% yield)

Workup

  1. stirringAfter stirring for 5 minutes
  2. stirringThe reaction mixture was stirred for 8 hours at room temperature
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe organic layer was washed with brine (100 mL)
  5. dry with materialdried over anhydrous sodium sulphate and evaporation

Sources & evidence

ORD record
ord-04e0e815df2440de965659909e59c70f
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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