Cyclohexylamine → HCID 19891245, compound

HRID 893866Notes

Reaction equation

HRID 893866 reaction equation
[C:1]([O:5][C:6]([C:8]1(C(O)=O)[S:20][C:11]23[CH:19]=[CH:18][CH:17]=[CH:16][C:12]2=[N:13][CH2:14][CH2:15][CH:10]3[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24]1(N)CC[CH2:27][CH2:26][CH2:25]1.C([N:33]([CH2:36][CH3:37])[CH2:34]C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:45])C=CC=CC=1>CN(C)C=O>[CH:36]1([NH:33][C:34]([CH:9]2[CH:10]3[C:11]4([CH:19]=[CH:18][CH:17]=[CH:16][C:12]4=[N:13][CH2:14][CH2:15]3)[S:20][CH:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:45])[CH2:37][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19960830HCID 19960830, compound

Product 1

HCID 19891245HCID 19891245, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 50 ml of dry dimethylformamide was dissolved 12.3 g of 2-tert-butoxycarbonyl-1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-carboxylic acid synthesized in Example 13, and 4.02 g of cyclohexylamine was further added thereto, followed by stirring for 30 minutes. Then 6.7 ml of triethylamine and a solution of 12.17 g of diphenylphosphorylazide in 10 ml of dry dimethylformamide were further added, and the resulting mixture was stirred at room temperature for one day. After dimethylformamide was distilled off under reduced pressure, the residue was dissolved in 300 ml of ethyl acetate, washed with 50 ml of an aqueous 5% sodium hydrogencarbonate solution three times, and then an aqueous 5% citric acid solution twice, and then a saturated aqueous sodium chloride solution twice, and then dried by sodium sulfate. Thereafter, ethyl acetate was distilled off under reduced pressure and the residue was purified by silica gel thin layer chromatography (developing solution: chloroform), whereby 9.17 g of N-cyclohexyl-2-tert-butoxycarbonyl-1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-3-carboamide was obtained (yield 60%).

Workup

  1. additionwas further added
  2. stirringthe resulting mixture was stirred at room temperature for one day
  3. distillationAfter dimethylformamide was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in 300 ml of ethyl acetate
  5. washwashed with 50 ml of an aqueous 5% sodium hydrogencarbonate solution three times
  6. dry with materialan aqueous 5% citric acid solution twice, and then a saturated aqueous sodium chloride solution twice, and then dried by sodium sulfate
  7. distillationThereafter, ethyl acetate was distilled off under reduced pressure
  8. customthe residue was purified by silica gel thin layer chromatography (developing solution: chloroform)

Sources & evidence

ORD record
ord-f0c927f3741b452fa99a81225fa51754
Source dataset
uspto-grants-1992_06
Patent number
US05126448

Reaction notes

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