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

m-Chloroperbenzoic acid → 4-[5-(3-Methyl-5-{[4-(methylsulfinyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one

HRID 1028138
Notes
Print preview

Reaction equation

HRID 1028138 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:17]2[S:21][C:20]([N:22]3[CH2:28][CH2:27][CH2:26][NH:25][C:24](=[O:29])[CH2:23]3)=[N:19][CH:18]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([S:15][CH3:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.ClC1C=CC=C(C(OO)=[O:38])C=1>ClCCl.[O-]S([O-])(=S)=O.[Na+].[Na+]>[CH3:1][C:2]1[CH:3]=[C:4]([C:17]2[S:21][C:20]([N:22]3[CH2:28][CH2:27][CH2:26][NH:25][C:24](=[O:29])[CH2:23]3)=[N:19][CH:18]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([S:15]([CH3:16])=[O:38])[CH:12]=[CH:11][N:10]=2)[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67239865HCID 67239865, compound

Product 1

HCID 532512384-[5-(3-Methyl-5-{[4-(methylsulfinyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-oneYield 6.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24477
Sodium Thiosulfate
Solvent

Procedure

To 4-[5-(3-methyl-5-{[4-(methylsulfanyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one (50 mg, 0.117 mmol) stirring in dichloromethane (586 μL) at room temperature was added 3-chloroperbenzoic acid (27.6 mg, 0.123 mmol). Stirred for 3 hr. at room temperature, diluted with 10% Na2S2O3 (aq.), and washed with sat. NaHCO3 (aq.) and brine. The organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. Purified by reverse phase preparative HPLC (0:100 to 95:5 acetonitrile:water: 0.1% v/v trifluoroacetic acid modifier) to afford 4-[5-(3-methyl-5-{[4-(methylsulfinyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one (3.3 mg, 7.5 μmol, 6.36% yield) as a yellow solid. MS APCI: [M+H]+ m/z 443.1. 1H NMR (500 MHz, CDCl3) δ 8.67 (d, J=4.9 Hz, 1H), 7.68 (s, 1H), 7.48 (s, 1H), 7.44 (d, J=4.9 Hz, 1H), 7.34-7.29 (m, 1H), 7.19 (s, 1H), 6.96 (s, 1H), 5.93-5.85 (m, 1H), 4.28 (s, 2H), 3.46 (s, 2H), 2.93 (s, 2H), 2.37 (s, 3H), 2.16-2.01 (m, 2H), 1.25 (s, 3H). rhSYK activity=+++.

Workup

  1. washwashed with sat. NaHCO3 (aq.) and brine
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurified by reverse phase preparative HPLC (0:100 to 95:5 acetonitrile:water: 0.1% v/v trifluoroacetic acid modifier)

Sources & evidence

ORD record
ord-c6a592f66590427bb1f81754e687aab0
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08735417B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes