Triethylamine → HCID 178453915, compound

HRID 1169589Notes

Reaction equation

HRID 1169589 reaction equation
Cl.Cl.[N:3]1([C:9]2[C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:12]=3[O:11][N:10]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[C:18]([O:22][C:23](=[O:34])[NH:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([CH2:31][CH:32]=O)[CH2:27][CH2:26]1)([CH3:21])([CH3:20])[CH3:19].CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:18]([O:22][C:23](=[O:34])[NH:24][C@H:25]1[CH2:26][CH2:27][C@H:28]([CH2:31][CH2:32][N:6]2[CH2:5][CH2:4][N:3]([C:9]3[C:13]4[CH:14]=[N:15][CH:16]=[CH:17][C:12]=4[O:11][N:10]=3)[CH2:8][CH2:7]2)[CH2:29][CH2:30]1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 67237571HCID 67237571, compoundHCID 178453924HCID 178453924, compound2×

Product 1

HCID 178453915HCID 178453915, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution in CH2Cl2 (10 ml) of 3-piperazin-1-yl-isoxazolo[4,5-c]pyridine dihydrochloride (840 mg, 3.0 mmol) and trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (904 mg, 3.7 mmol; intermediate H; prepared according to WO2007/093540) was treated with Et3N (629 mg, 6.2 mmol) before addition of Na(AcO)3BH (1.03 g, 5 mmol). The reaction mixture was stirred 16 h at r.t., then sat. aq. NaHCO3 was added and the product was extracted with 2 portions of CH2Cl2. After drying (MgSO4) and evaporation of the solvent the product was purified by flash chromatography (50 g SiO2, EtOAc/MeOH 100:0→80:20) to obtain 930 mg (71%) of the title compound as an off white solid. m/z=430.3 ([M+H]+).

Workup

  1. extractionthe product was extracted with 2 portions of CH2Cl2
  2. customAfter drying
  3. custom(MgSO4) and evaporation of the solvent the product
  4. customwas purified by flash chromatography (50 g SiO2, EtOAc/MeOH 100:0→80:20)

Sources & evidence

ORD record
ord-559d2d17a0874660ade7457a0f51cc54
Source dataset
uspto-grants-2010_11
Patent number
US07825123B2

Reaction notes

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