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m-Chloroperbenzoic acid → HCID 90308809, compound

HRID 2283664
Notes
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Reaction equation

HRID 2283664 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[S:12]1[CH:16]=[CH:15][C:14]2[C:17]([NH:21][C:22]3[N:23]=[C:24](SC)[N:25]=[N:26][C:27]=3[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:18][CH:19]=[CH:20][C:13]1=2.[C:35]([O:39][C:40](=[O:49])[NH:41][C@H:42]1[CH2:47][CH2:46][CH2:45][CH2:44][C@H:43]1[NH2:48])([CH3:38])([CH3:37])[CH3:36].C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl.C(OCC)(=O)C>[S:12]1[CH:16]=[CH:15][C:14]2[C:17]([NH:21][C:22]3[N:23]=[C:24]([NH:48][C@@H:43]4[CH2:44][CH2:45][CH2:46][CH2:47][C@@H:42]4[NH:41][C:40]([O:39][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:49])[N:25]=[N:26][C:27]=3[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:18][CH:19]=[CH:20][C:13]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 90308829HCID 90308829, compound

Product 1

HCID 90308809HCID 90308809, compound

Reagents, catalysts & solvents 2

HCID 6212
Chloroform
Solvent
2×
HCID 8857Ethyl AcetateSolvent

Procedure

A solution of m-CPBA (65 mg) in chloroform (1.5 ml) was added to a solution of ethyl 5-(benzo[b]thiophen-4-ylamino)-3-(methylthio)-1,2,4-triazine-6-carboxylate obtained in the above-described Step 1 (33 mg) in chloroform (1.5 ml), the reaction solution was stirred at room temperature for 10 minutes. Thereafter, tert-butyl((1S,2R)-2-aminocyclohexyl)carbamate (60 mg) and diisopropylethylamine (0.10 ml) were added, and then the reaction solution was stirred at room temperature for 3 hours. The reaction solution was diluted with ethyl acetate and then washed successively with an aqueous sodium bicarbonate solution and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum, and then the resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain ethyl 5-(benzo[b]thiophen-4-ylamino)-3-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-1,2,4-triazine-6-carboxylate.

Workup

  1. stirringthe reaction solution was stirred at room temperature for 3 hours
  2. washwashed successively with an aqueous sodium bicarbonate solution
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under vacuum
  5. customthe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-382a6ce8351a46e9ae0e951a7ee9560e
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145414B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes