Methanol → HCID 178468197, compound

HRID 1373022Notes

Reaction equation

HRID 1373022 reaction equation
[C:1](#N)[CH3:2].C[OH:5].[Cl:6]CC([N:10]1[C@H:14]([C:15]#[N:16])[CH2:13][S:12][CH2:11]1)=O.[N+:17]([C:20]1[CH:21]=[CH:22][C:23]([NH:26][C@H:27]2[CH2:32][CH2:31][C@H:30]([NH2:33])[CH2:29][CH2:28]2)=[N:24][CH:25]=1)([O-:19])=[O:18]>C(OCC)(=O)C.C(Cl)(Cl)Cl.CCOCC.O>[ClH:6].[ClH:6].[C:15]([CH:14]1[CH2:13][S:12][C@H:11]([C:1](=[O:5])[CH3:2])[N:10]1[NH:33][C@H:30]1[CH2:29][CH2:28][C@H:27]([NH:26][C:23]2[CH:22]=[CH:21][C:20]([N+:17]([O-:19])=[O:18])=[CH:25][N:24]=2)[CH2:32][CH2:31]1)#[N:16]

Participants

9

Reactant 4

HCID 887MethanolHCID 6342AcetonitrileHCID 55265408(4R)-3-(chloroacetyl)-1,3-thiazolidine-4-carbonitrileHCID 178511612HCID 178511612, compound

Product 1

HCID 178468197HCID 178468197, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2 ml of acetonitrile-1 ml of methanol containing 100 mg of (R)-3-chloroacetyl-4-cyanothiazolidine (the compound of Reference Example 2 mentioned below) and 372 mg of N-(5-nitro-2-pyridyl)-trans-1,4-cyclohexanediamine was stirred at room temperature for 15 hours. Water was added to the reaction mixture and the mixture was extracted with chloroform. After the extract was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by diol column chromatography (solvent: 0 to 5% methanol-chloroform) to obtain an oily product. The oily product was dissolved in 0.5 ml of ethyl acetate-0.5 ml of chloroform, and 1.0 ml of 2N hydrochloric acid-ether was added thereto, followed by 2 ml of ether. Precipitates were collected by filtration and washed with ether to obtain 173 mg of (R)-4-cyano-3-[trans-4-(5-nitro-2-pyridylamino)cyclohexylamino]-acetylthiazolidine-dihydrochloride (Example 4-1 in Table 4).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialAfter the extract was dried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by diol column chromatography (solvent: 0 to 5% methanol-chloroform)
  5. customto obtain an oily product
  6. additionwas added
  7. customPrecipitates
  8. filtrationwere collected by filtration
  9. washwashed with ether

Sources & evidence

ORD record
ord-f61fdae7d2ab43599905c9bdbedf444f
Source dataset
uspto-grants-2007_01
Patent number
US07160877B2

Reaction notes

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