Acetic Acid → HCID 25204730, compound

HRID 515569Notes

Reaction equation

HRID 515569 reaction equation
C(O)(=O)C.C(O[C:8]1(O[Si](C)(C)C)[CH2:10][CH2:9]1)C.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[N:27][N:26]3[C:37]=2[C:38]2[CH:43]=[CH:42][N:41]=[N:40][CH:39]=2)=[CH:19][CH:18]=1.C([BH3-])#N.[Na+]>CO.O1CCCC1>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH2:32][CH2:33][N:34]([CH:8]5[CH2:10][CH2:9]5)[CH2:35][CH2:36]4)=[N:27][N:26]3[C:37]=2[C:38]2[CH:43]=[CH:42][N:41]=[N:40][CH:39]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 25204668HCID 25204668, compound

Product 1

HCID 25204730HCID 25204730, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

0.15 ml of acetic acid and 0.32 ml (1.6 mmol) of (1-ethoxycyclopropoxy)trimethylsilane are added, in a reactor, to 0.10 g (0.27 mmol) of 2-(4-fluorophenyl)-6-(piperazin-1-yl)-3-(pyridazin-4-yl)imidazo[1,2-b]pyridazine in 3 ml of methanol. 1.2 ml (1.2 mmol) of a molar solution of sodium cyanoborohydride in tetrahydrofuran are then added. After stirring for 15 minutes, the mixture is heated at 50° C. for 2 hours. After cooling, the product is extracted with dichloromethane, and the organic phase is filtered over a hydrophobic cartridge and then concentrated under reduced pressure. The residue is chromatographed on a silica gel column, to give 0.064 g of product. The latter is crystallized from diisopropyl ether, to give 0.053 g of light yellow crystals after drying.

Workup

  1. temperatureAfter cooling
  2. extractionthe product is extracted with dichloromethane
  3. filtrationthe organic phase is filtered over a hydrophobic cartridge
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on a silica gel column

Sources & evidence

ORD record
ord-4aedd24792b84e5b8c4bd2534a3a6959
Source dataset
uspto-grants-2015_08
Patent number
US09108971B2

Reaction notes

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