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Methanol → HCID 178478703, compound

HRID 22935
Notes
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Reaction equation

HRID 22935 reaction equation
C(#N)C.CO.[Cl:6][CH2:7][C:8]([N:10]1[C@H:14]([C:15]#[N:16])[CH2:13][S:12][CH2:11]1)=[O:9].[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]([C@@H:14]1[CH2:13][S:12][CH2:11][N:10]1[C:8](=[O:9])[CH2:7][NH:33][C@H:30]1[CH2:31][CH2:32][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)[CH2:28][CH2:29]1)#[N:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

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

Product 1

HCID 178478703HCID 178478703, compound

Reagents, catalysts & solvents 4

HCID 962
Water
Solvent
HCID 3283Diethyl EtherSolvent
HCID 6212ChloroformSolvent
HCID 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-c2eceec73ba2418f935e9c3c291606f9
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06849622B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes