4-Methylmorpholine → HCID 67102060, compound

HRID 2080435Notes

Reaction equation

HRID 2080435 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[N:16]=[C:15]([CH2:17][C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[C:14]([CH2:26][CH2:27][C:28](O)=[O:29])=[CH:13][C:12]=2[F:31])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.N1(O)C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[N:16]=[C:15]([CH2:17][C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[C:14]([CH2:26][CH2:27][C:28]([N:36]3[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]3)=[O:29])=[CH:13][C:12]=2[F:31])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 671017493-[6-(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl-5-fluoropyridin-3-yl]propionic acid

Product 1

HCID 67102060HCID 67102060, compoundYield 181%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a dichloromethane (3 ml) solution of 3-[6-(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl-5-fluoropyridin-3-yl]propionic acid (100 mg, 0.21 mmol) were added 1-methylpiperazine (0.026 ml, 0.23 mmol), benzotriazol-1-ol (32 mg, 0.23 mmol), 4-methylmorpholine (0.026 ml, 0.23 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (45 mg, 0.23 mmol) at room temperature. The resulting mixture was stirred at room temperature for 16 hours. After the reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate, the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. The fraction obtained from the dichloromethane:methanol=19:1 eluate was concentrated under reduced pressure. The residue was dissolved in ethanol (3 ml), followed by the addition of 1N hydrochloric acid (0.224 ml). After stirring at room temperature for 30 minutes, the reaction mixture was concentrated under reduced pressure. The residue thus obtained was washed with ethanol and collected by filtration to give the title compound (111 mg, 0.19 mmol, 89%) as a white solid.

Workup

  1. washAfter the reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationmethanol=19:1 eluate was concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethanol (3 ml)
  8. additionfollowed by the addition of 1N hydrochloric acid (0.224 ml)
  9. stirringAfter stirring at room temperature for 30 minutes
  10. concentrationthe reaction mixture was concentrated under reduced pressure
  11. customThe residue thus obtained
  12. washwas washed with ethanol
  13. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2856fc918fe6488fa553cea5e186ba5f
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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