Acetic Acid → HCID 68999681, compound

HRID 1821331Notes

Reaction equation

HRID 1821331 reaction equation
[CH:1]([C:3]1[CH:28]=[CH:27][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2/[CH:16]=[CH:17]/[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][N:19]=2)=[O:8])=[CH:5][CH:4]=1)=O.C(O)(=O)C.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O>[NH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](/[CH:17]=[CH:16]/[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:7](=[O:8])[C:6]2[CH:27]=[CH:28][C:3]([CH2:1][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:4][CH:5]=2)=[N:19]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 86628199HCID 86628199, compound

Product 1

HCID 68999681HCID 68999681, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

(E)-4-Formyl-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}benzamide (60 mg, 0.16 mmol) was dissolved in dichloroethane (1.5 mL) and acetic acid (10 μL) and morpholine (22 μL) and sodium triacetoxyborohydride (104 mg, 0.49 mmol) were added thereto. The mixture was stirred at room temperature for 20 hours, added with water and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated in ethyl acetate to obtain Compound 80 (21 mg, 30%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was triturated in ethyl acetate

Sources & evidence

ORD record
ord-cda3928cb9824a098fb1cf2115373879
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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