Triethylamine → HCID 59170237, compound

HRID 1446291Notes

Reaction equation

HRID 1446291 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([OH:15])=O.Cl.[F:17][C:18]1[CH:31]=[CH:30][C:21]([C:22]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[O:23])=[CH:20][CH:19]=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>ClCCl>[F:17][C:18]1[CH:31]=[CH:30][C:21]([C:22]([CH:24]2[CH2:29][CH2:28][N:27]([C:13]([C:3]3[C:4]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)=[N:5][O:6][C:2]=3[CH3:1])=[O:15])[CH2:26][CH2:25]2)=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Product 1

HCID 59170237HCID 59170237, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Methyl-3-phenylisooxazole-4-carboxylic acid (40 mg, 0.197 mmol), 4-(4-Fluorobenzoyl)piperidine hydrochloride (31.4 mg, 0.151 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (37.7 mg, 0.197 mmol) and triethylamine (59.8 mg, 0.591 mmol) were mixed in dichloromethane (2 ml) and stirred at room temperature over night. Solvent was evaporated in vacuo, and the residue was taken up in methanol (1 mL), filtered and purified by preparative chromatography. The fractions were partitioned between NaHCO3 (sat) and ethylacetate. The organic layer was washed with water and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C23H21FN2O3: 392.1536, found 392.1542.

Workup

  1. customSolvent was evaporated in vacuo
  2. filtrationfiltered
  3. custompurified by preparative chromatography
  4. customThe fractions were partitioned between NaHCO3 (sat) and ethylacetate
  5. washThe organic layer was washed with water
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa56b3905e4e470f82f6c58d6c466a93
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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