Acetic Acid → HCID 24947011, compound

HRID 1454239Notes

Reaction equation

HRID 1454239 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:17]=[CH:16][C:8]([C:9]([NH:11][CH2:12][CH2:13][NH:14][CH3:15])=[O:10])=[CH:7][C:6]=1[O:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[CH3:3].[CH2:25](OC1(O[Si](C)(C)C)CC1)[CH3:26].[CH3:36]C(O)=O.[BH3-]C#N.[Na+]>CO.C1COCC1>[CH:15]1([N:14]([CH3:36])[CH2:13][CH2:12][NH:11][C:9](=[O:10])[C:8]2[CH:16]=[CH:17][C:5]([CH2:4][N:2]([CH3:3])[CH3:1])=[C:6]([O:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:7]=2)[CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 57530054HCID 57530054, compound

Product 1

HCID 24947011HCID 24947011, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-dimethylaminomethyl-N-(2-methylamino-ethyl)-3-(pyridin-3-yloxy)-benzamide (0.090 g, 0.274 mmol) in a 1:1 mixture of THF:MeOH (4 mL) was added [(1-ethoxycyclopropyl)-oxy]trimethylsilane (0.28 mL, 1.37 mmol), AcOH (0.08 mL, 1.37 mmol), and NaCNBH3 (0.088 g, 1.37 mmol). The reaction mixture was heated to 50° C. for 24 h, cooled to rt and concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (15 mL), washed with sat. NaHCO3 (5 mL), dried (Na2SO4), and concentrated. HPLC purification under basic conditions yielded the desired product (0.036 g, 38%). MS (ESI): m/z found, 369.2 [M+H]+.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2 (15 mL)
  4. washwashed with sat. NaHCO3 (5 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customHPLC purification under basic conditions

Sources & evidence

ORD record
ord-e1cdc963fd204e15a82ec401da58f4d2
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

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