Acetic Acid → HCID 69001475, compound

HRID 1821373Notes

Reaction equation

HRID 1821373 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.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(O)(=O)C.[BH4-].[Na+]>ClC(Cl)C>[N:25]1([CH2:23][C:20]2[CH:21]=[CH:22][N:18]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3/[CH:11]=[CH:10]/[C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][N:2]=3)[CH:19]=2)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 4311764Sodium borohydrideHCID 86628206HCID 86628206, compound

Product 1

HCID 69001475HCID 69001475, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Compound 167 (0.08 g, 0.26 mmol) was dissolved in dichloroethane (2.0 mL) and the solution was added with morpholine (67 μL, 0.77 mmol), acetic acid (84 μL, 0.77 mmol) and sodium borohydride (0.16 g, 0.77 mmol) followed by stirring at room temperature for 30 minutes. The reaction mixture was extracted with ethyl acetate, the organic layer was concentrated and the residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to obtain Compound 182 (0.04 g, 41%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. concentrationthe organic layer was concentrated
  3. customthe residue was purified by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-dc75f2fc530147b29cf72ccd598ddab8
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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