Triethylamine → HCID 11743912, compound

HRID 1392423Notes

Reaction equation

HRID 1392423 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([NH:9][C:10]2([C:16]([NH:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[NH2:31])[CH2:21][CH:20]3[OH:32])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])[CH:3]=1.C(N(CC)CC)C>CS(C)=O.C(OCC)(=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([NH:9][C:10]2([C:16]([NH:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[NH2:31])[CH2:21][C:20]3=[O:32])=[O:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)=[O:8])[CH:3]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 69310363HCID 69310363, compound

Product 1

HCID 11743912HCID 11743912, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 4-[N-[1-[N-(5-methyl-isoxazol-3-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-aminophenyl)piperidin-3-ol (1.1 g) obtained in Step 1 in 5 ml of dimethyl sulfoxide, was added 1.2 ml of triethylamine. The reaction mixture was cooled to 0° C. Pyridine-SO3 complex (0.9 g) was added to the reaction mixture, which was then stirred for about 4 hours at room temperature. The reaction mixture was diluted with 20 ml of ethyl acetate and washed with brine. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was filtered and dried to give 820 mg of the titled compound as white color.

Workup

  1. additionPyridine-SO3 complex (0.9 g) was added to the reaction mixture, which
  2. washwashed with brine
  3. customThe resulting organic layer was dried
  4. concentrationconcentrated on sodium sulfate
  5. filtrationThe resulting residue was filtered
  6. customdried

Sources & evidence

ORD record
ord-278523ab36094d5585878d2428ac71ca
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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