4-Methylmorpholine → HCID 57736511, compound

HRID 1641727Notes

Reaction equation

HRID 1641727 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.Cl.[CH2:31]([O:33][C:34](=[O:38])[CH2:35][CH2:36][NH2:37])[CH3:32].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1>C(Cl)Cl>[CH2:31]([O:33][C:34](=[O:38])[CH2:35][CH2:36][NH:37][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])[CH3:32]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 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 57736511HCID 57736511, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid (106 mg, 0.252 mmol) obtained in Example 12 in methylene chloride (3 ml), β-alanine ethyl ester hydrochloride (46 mg, 0.302 mmol), 1-hydroxybenzotriazole (34 mg, 0.252 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride mg, 0.302 mmol) and 4-methylmorpholine (66 μl, 0.604 mmol) were added. The reaction solution was stirred for 15 hours at room temperature, and 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:ethyl acetate (=1:1) was concentrated under reduced pressure, to obtain the title compound (126 mg, 0.242 mmol, 96%) as an amorphous substance.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. concentrationThe resulting concentration residue
  3. customthe fraction obtained from an elution with hexane
  4. concentrationethyl acetate (=1:1) was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a4faf0359b7b4653808b4caffbd88b68
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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