HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

(1S)-(+)-Camphor-10-sulphonic acid → 4-(1-Methylazetidin-3-yl)piperazine-1-carboxylic acid {4-[4-(3-phenylacetylthioureido)phenoxy]pyridin-2-yl}amide

HRID 492967
Notes
Print preview

Reaction equation

HRID 492967 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]3[CH2:21][CH2:20][N:19]([CH:22]4[CH2:25][N:24]([CH3:26])[CH2:23]4)[CH2:18][CH2:17]3)=[O:15])[CH:8]=2)=[CH:4][CH:3]=1.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[C:44]1([CH2:50][C:51]([N:53]=[C:54]=[S:55])=[O:52])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(=O)([O-])O.[Na+]>C(O)C.C1(C)C=CC=CC=1.CCCCCC.C(OCC)C.C(OCC)(=O)C.O1CCCC1>[C:44]1([CH2:50][C:51]([NH:53][C:54](=[S:55])[NH:1][C:2]2[CH:28]=[CH:27][C:5]([O:6][C:7]3[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]4[CH2:21][CH2:20][N:19]([CH:22]5[CH2:23][N:24]([CH3:26])[CH2:25]5)[CH2:18][CH2:17]4)=[O:15])[CH:8]=3)=[CH:4][CH:3]=2)=[O:52])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

11

Reactant 4

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 516892Sodium BicarbonateHCID 12454157Phenylacetyl isothiocyanateHCID 576774204-(1-Methylazetidin-3-yl)piperazine-1-carboxylic acid [4-(4-aminophenoxy)pyridin-2-yl]amide

Product 1

HCID 576776394-(1-Methylazetidin-3-yl)piperazine-1-carboxylic acid {4-[4-(3-phenylacetylthioureido)phenoxy]pyridin-2-yl}amide
Yield 23.3%

Reagents, catalysts & solvents 6

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(1-methylazetidin-3-yl)piperazine-1-carboxylic acid [4-(4-aminophenoxy)pyridin-2-yl]amide (130 mg) in ethanol (6.0 ml)-tetrahydrofuran (6.0 ml) was added (1S)-(+)-10-camphorsulfonic acid (150 mg), followed by stirring at room temperature for 15 min. A solution of 2-phenylacetyl isothiocyanate in toluene (0.25 M, 4.08 ml) was added to the reaction mixture, followed by stirring at room temperature for 2 hrs. Ethyl acetate (50 ml) and a saturated aqueous solution of sodium hydrogencarbonate (20 ml) were added to the reaction mixture, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated to give a residue, which was then purified by silica gel column chromatography (FUJI Silysia NH, eluent; ethyl acetate, then ethyl acetate:methanol=20:1). Fractions containing the titled compound were concentrated to give a residue, to which diethyl ether (5 ml) and hexane (10 ml) were added to give a precipitate. The precipitate was suspended in the solvent. Then the precipitate was filtered off, washed with hexane, and dried under aeration to provide the titled compound (44.3 mg, 23.3%) as pale yellow powder.

Workup

  1. stirringby stirring at room temperature for 2 hrs
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe organic layer was concentrated
  7. customto give a residue, which
  8. customwas then purified by silica gel column chromatography (FUJI Silysia NH, eluent
  9. additionFractions containing the titled compound
  10. concentrationwere concentrated
  11. customto give a residue
  12. customto give a precipitate
  13. filtrationThen the precipitate was filtered off
  14. washwashed with hexane
  15. customdried under aeration

Sources & evidence

ORD record
ord-b4d13e30849b43059ce99ded8aaa95e8
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07531532B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes