4-Methylmorpholine → HCID 58734275, compound

HRID 2080445Notes

Reaction equation

HRID 2080445 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[C:12]2[N:17]=[C:16]([NH2:18])[CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CN1CCOCC1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.[N:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[CH2:63][C:64](O)=[O:65]>ClCCl.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[C:12]2[N:17]=[C:16]([NH:18][C:64](=[O:65])[CH2:63][C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][N:57]=3)[CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 231147766-[(4-Chlorobenzene-1-sulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-amine

Product 1

HCID 58734275HCID 58734275, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

To a dichloromethane (5 ml) solution of 6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-ylamine (74 mg, 0.187 mmol) were added N-methylmorpholine (90 μl, 0.818 mmol), 1-hydroxybenzotriazole (11 mg, 0.313 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (60 mg, 0.312 mmol) and 2-pyridylacetic acid hydrochloride (54 mg, 0.312 mmol). The resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted with dichloromethane. The diluted solution was washed sequentially with water, a saturated aqueous solution of sodium bicarbonate and brine. The organic layer thus obtained was dried over magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=4:1 eluate was concentrated under reduced pressure to give the title compound (48 mg, 0.0934 mmol, 50%) as a white amorphous substance.

Workup

  1. washThe diluted solution was washed sequentially with water
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationethyl acetate=4:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8e445f661b4640c6830f356b6914fd17
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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