Water → HCID 178505144, compound

HRID 2042416Notes

Reaction equation

HRID 2042416 reaction equation
Cl.Cl.Cl.[O:4]1[C:12]2[CH:11]=[CH:10][N:9]=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[CH:6]=[CH:5]1.CCN(CC)CC.[CH3:35][S:36](Cl)(=[O:38])=[O:37].O>C(Cl)Cl>[O:4]1[C:12]2[CH:11]=[CH:10][N:9]=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH:27][S:36]([CH3:35])(=[O:38])=[O:37])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[CH:6]=[CH:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178478592HCID 178478592, compound2×

Product 1

HCID 178505144HCID 178505144, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

trans-4-[2-(4-Furo[3,2-c]pyridin-4-yl-piperazin-1-yl)-ethyl]-cyclohexylamine trihydrochloride (intermediate A) (150 mg, 0.34 mmol) was dissolved in CH2Cl2 (1.5 ml) and the solution was cooled to 0° C. Et3N (139 mg, 1.37 mmol) and methanesulfonyl chloride (78 mg, 0.68 mmol) were added and the reaction mixture was stirred over night at room temperature. H2O was added and the product was extracted with CH2Cl2. The organic layer was dried (Na2SO4) and the solvent was evaporated. Purification by flash chromatography over silica gel (CH2Cl2/MeOH/25% NH3 aq 140:10:1) yielded the title compound as a white solid (78 mg, 56%), MS (ISP) m/z=407.2 [(M+H)+].

Workup

  1. extractionthe product was extracted with CH2Cl2
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe solvent was evaporated
  4. customPurification by flash chromatography over silica gel (CH2Cl2/MeOH/25% NH3 aq 140:10:1)

Sources & evidence

ORD record
ord-edbaa63a360d4142af2424c76540eabd
Source dataset
uspto-grants-2013_11
Patent number
US08586579B2

Reaction notes

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