Acetic Acid → HCID 69001297, compound

HRID 1821379Notes

Reaction equation

HRID 1821379 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.[CH:25]1([CH2:28][NH2:29])[CH2:27][CH2:26]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O>[CH:25]1([CH2:28][NH:29][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)[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 75646CyclopropanemethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 86628206HCID 86628206, compound

Product 1

HCID 69001297HCID 69001297, compoundYield 14.3%

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 cyclopropanemethylamine (50 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 189 (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-8d12aef610ae4e08a6feb3370d8cd3e9
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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