Acetic Acid → HCID 10222270, compound

HRID 1357486Notes

Reaction equation

HRID 1357486 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[CH:18][CH:17]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.C(O[C:35]1(O[Si](C)(C)C)[CH2:37][CH2:36]1)C.C([BH3-])#N.[Na+]>CO>[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[NH:15][C:16]2[CH:17]=[CH:18][C:19]([N:22]4[CH2:27][CH2:26][N:25]([CH:35]5[CH2:37][CH2:36]5)[CH2:24][CH2:23]4)=[CH:20][CH:21]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 12370530HCID 12370530, compound

Product 1

HCID 10222270HCID 10222270, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

35 mg (0.10 mmol) of 9-[4-(piperazin-1-yl)phenyl]aminoacridine (Example 16) was dissolved in 1 ml of methanol. 57 μl (1.0 mmol) of acetic acid, 22 μl (0.11 mmol) of (1-ethoxycyclopropyloxy)-trimethylsilane and a small amount of 3 Å molecular sieves were added. The reaction mixture was stirred at room temperature under nitrogen atmosphere. After 30 min 28 mg (0.45 mmol) of sodium cyanoborohydride was added and the reaction mixture was heated at 50° C. over night. The solvents were removed under vacuum, and the residue was purified by chromatography (silica gel column, eluent chloroform/methanol 6:1) to obtain 3.8 mg (10%, overall yield 2%) of the title compound.

Workup

  1. temperaturethe reaction mixture was heated at 50° C. over night
  2. customThe solvents were removed under vacuum
  3. customthe residue was purified by chromatography (silica gel column, eluent chloroform/methanol 6:1)

Sources & evidence

ORD record
ord-7c387094b89f4d68a635b3442047cdcf
Source dataset
uspto-grants-2003_07
Patent number
US06593324B2

Reaction notes

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