Sodium Hydroxide → HCID 67428977, compound

HRID 1887091Notes

Reaction equation

HRID 1887091 reaction equation
[ClH:1].[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[N:14][CH:13]=[CH:12]3)[CH2:4][CH2:3]1.C(O[C:22]1(O[Si](C)(C)C)[CH2:24][CH2:23]1)C.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C.C(N(CC)CC)C>[ClH:1].[CH:22]1([N:2]2[CH2:7][CH2:6][CH:5]([O:8][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][CH:18]=3)[CH:15]=[N:14][CH:13]=[CH:12]4)[CH2:4][CH2:3]2)[CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 674289666-(Piperidin-4-yloxy)-isoquinoline hydrochloride

Product 1

HCID 67428977HCID 67428977, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

300 mg (1.13 mmol) 6-(Piperidine-4-yloxy)-isoquinoline hydrochloride (124) are dissolved in 10 mL of methanol. 202 mg of triethylamine, molecular sieves 4A, 600 mg of glacial acetic acid, 871 mg of (1-Ethoxy-cyclopropyloxy)-trimethyl-silane and 101 mg of sodium cyanoborohydride are added successively and the reaction mixture is heated under reflux for 6 hours. The reaction mixture is cooled to room temperature, 6 mL of 2N sodium hydroxide are added and the reaction mixture is filtered. The filtrate is evaporated, the residue is taken up in dichloromethane, extracted with 2 N sodium hydroxide and brine, dried with sodium sulfate, evaporated to dryness and the crude material is purified by preparative HPLC. The product fractions are evaporated, the product is taken up in 2 N hydrochloric acid and lyophilized.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 6 hours
  3. filtrationthe reaction mixture is filtered
  4. customThe filtrate is evaporated
  5. extractionextracted with 2 N sodium hydroxide and brine
  6. dry with materialdried with sodium sulfate
  7. customevaporated to dryness
  8. customthe crude material is purified by preparative HPLC
  9. customThe product fractions are evaporated

Sources & evidence

ORD record
ord-494b77e2002b424dae90b060b9ba8090
Source dataset
uspto-grants-2013_08
Patent number
US08501736B2

Reaction notes

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