Acetic Acid → HCID 69004378, compound

HRID 1821376Notes

Reaction equation

HRID 1821376 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19]2)=[N:2]1.[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28][NH2:29].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[CH:22]=[CH:21][C:20]([CH2:23][NH:29][CH2:28][CH2:27][N:26]([CH3:30])[CH3:25])=[CH:19]2)=[N:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 86628206HCID 86628206, compound

Product 1

HCID 69004378HCID 69004378, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Compound 167 (0.06 g, 0.19 mmol) was dissolved in dichloroethane (2.0 mL) and the solution was added with N,N-dimethylethylenediamine (62 μL, 0.57 mmol), acetic acid (63 μL, 0.57 mmol) and sodium triacetoxyborohydride (0.12 g, 0.57 mmol), followed by stirring at room temperature for 1 hour. The reaction mixture was added with water, extracted with ethyl acetate and the organic layer was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/methanol=9/1) to obtain Compound 186 (0.01 g, 14%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationthe organic layer was concentrated
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol=9/1)

Sources & evidence

ORD record
ord-6454ac4d023847ca8f1b8faccde1039c
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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