Sodium Thiosulfate → 4-[5-(3-Methyl-5-{[4-(methylsulfonyl)-2-pyrimidinyl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one

HRID 1028135Notes

Reaction equation

HRID 1028135 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](SC)[CH:12]=[CH:11][N:10]=2)[CH:7]=1.Cl[C:31]1C=CC=C(C(OO)=O)C=1.[O-:41][S:42]([O-:45])(=S)=O.[Na+].[Na+]>ClCCl>[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:10]=[C:11]([S:42]([CH3:31])(=[O:45])=[O:41])[CH:12]=[CH:13][N:14]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 67239865HCID 67239865, compound

Product 1

HCID 672408554-[5-(3-Methyl-5-{[4-(methylsulfonyl)-2-pyrimidinyl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-oneYield 18.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-[5-(3-methyl-5-{[4-(methylsulfanyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one (0.94 g, 2.204 mmol) stirring in dichloromethane (11 mL) at room temperature was added 3-chloroperbenzoic acid (1.587 g, 7.08 mmol). Stirred for 4 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 CombiFlash (100:0 to 0:20 dichloromethane:methanol) to afford impure 4-[5-(3-methyl-5-{[4-(methylsulfonyl)-2-pyrimidinyl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one (0.188 g, 0.411 mmol, 18.6% yield) as an orange solid (contaminated with starting material). MS APCI: [M+H]+ m/z 459.1

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 CombiFlash (100:0 to 0:20 dichloromethane:methanol)

Sources & evidence

ORD record
ord-8c0ff5855dcb4766a6ca98c360539952
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

Loading…