m-Chloroperbenzoic acid → HCID 24950907, compound

HRID 625078Notes

Reaction equation

HRID 625078 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[NH2:12][C@H:13]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[C:23]3[CH2:30][S:29][CH2:28][C:24]=3[N:25]=[CH:26][N:27]=2)[CH2:18][CH2:17]1)=[O:15]>C(Cl)Cl.CO>[NH2:12][C@H:13]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[C:23]3[CH2:30][S:29](=[O:9])[CH2:28][C:24]=3[N:25]=[CH:26][N:27]=2)[CH2:18][CH2:17]1)=[O:15]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 24949764HCID 24949764, compound

Product 1

HCID 24950907HCID 24950907, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

m-CPBA (77%, 67 mg, 0.30 mmol) was added to a solution of (R)-2-amino-3-(4-chlorophenyl)-1-(4-(5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one (120 mg, 0.30 mmol) in DCM (10 mL) and MeOH (1 mL). The mixture was stirred at room temperature for 2 hours. The solvent was removed, and the residue was subject to column chromatography, eluted by DCM/MeOH (4:1-1:1) to afford (R)-2-amino-3-(4-chlorophenyl)-1-(4-(6-oxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one (21 mg, 17%) as the free amine. LCMS: 420.2 [M+H+] (APCI+).

Workup

  1. customThe solvent was removed
  2. washeluted by DCM/MeOH (4:1-1:1)

Sources & evidence

ORD record
ord-63bea08259214a75a2ff5783a5c81d6f
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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