4-Methylmorpholine → HCID 57736512, compound

HRID 1641728Notes

Reaction equation

HRID 1641728 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16](O)=[O:17])=[N:14][CH:15]=1.[NH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1>C(Cl)Cl.C(OCC)(=O)C>[C:36]([O:35][C:34](=[O:40])[NH:33][CH2:32][CH2:31][NH:30][C:16]([C:13]1[CH:12]=[C:11]([CH3:19])[C:10]([CH:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[S:20]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)(=[O:21])=[O:22])=[CH:15][N:14]=1)=[O:17])([CH3:37])([CH3:39])[CH3:38]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 187201N-BOC-ethylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 577364395-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid

Product 1

HCID 57736512HCID 57736512, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid (374 mg, 0.888 mmol) obtained in Example 12 in methylene chloride (10 ml), tert-butyl (2-aminoethyl)carbamate (170 μl, 1.07 mmol), 1-hydroxybenzotriazole (120 mg, 0.888 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (206 mg, 1.07 mmol) and 4-methylmorpholine (116 μl, 1.07 mmol) were added, and the mixture was stirred for 19 hours at room temperature. Ethyl acetate was added to the reaction solution, and the mixture was washed sequentially with saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting concentration residue was subjected to silica gel column chromatography, and the fraction obtained from an elution with hexane:ethylacetate (=1:1) was concentrated under reduced pressure, to obtain the title compound (491 mg, 0.871 mmol, 98%) as an amorphous substance.

Workup

  1. washthe mixture was washed sequentially with saturated aqueous sodium hydrogencarbonate and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. concentrationThe resulting concentration residue
  6. customthe fraction obtained from an elution with hexane
  7. concentrationethylacetate (=1:1) was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1bc2a4a50d68440e9a130cd448cea56c
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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