Acetic Acid → HCID 178474985, compound

HRID 1169591Notes

Reaction equation

HRID 1169591 reaction equation
Cl.Cl.[O:3]1[C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C@H:20]3[CH2:25][CH2:24][C@H:23]([NH2:26])[CH2:22][CH2:21]3)[CH2:14][CH2:13]2)=[N:4]1.[CH3:27][C:28](O)=[O:29].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>O1CCOCC1>[O:3]1[C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[C:5]([N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][C@H:20]3[CH2:25][CH2:24][C@H:23]([NH:26][C:28](=[O:29])[CH3:27])[CH2:22][CH2:21]3)[CH2:16][CH2:17]2)=[N:4]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178478719HCID 178478719, compound

Product 1

HCID 178474985HCID 178474985, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture in dioxane (5 ml) of trans-4-[2-(4-isoxazolo[4,5-c]pyridin-3-yl-piperazin-1-yl)-ethyl]-cyclohexylamine dihydrochloride (100 mg, 0.25 mmol), AcOH (22 mg, 0.37 mmol), iPr2NEt (161 mg, 1.2 mmol) and TBTU (96 mg, 0.30 mmol) was stirred 16 h at r.t. After evaporation to dryness sat. aq. NaHCO3 was added and the product was extracted with 2 portions of CH2Cl2. The organic layers were directly loaded on a column. Flash chromatography (20 g SiO2, CH2Cl2/MeOH 100:0→90:10) yielded 62 mg (67%) of the title compound as white solid. m/z=372.2 ([M+H]+).

Workup

  1. customAfter evaporation to dryness sat. aq. NaHCO3
  2. additionwas added
  3. extractionthe product was extracted with 2 portions of CH2Cl2

Sources & evidence

ORD record
ord-f41867cb9e0a4d949ad9719968d9a150
Source dataset
uspto-grants-2010_11
Patent number
US07825123B2

Reaction notes

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