m-Chloroperbenzoic acid → HCID 59427316, compound

HRID 1013781Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][C:26]4[C:35]5[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][N:34]=5)[N:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:46])C=1>C(Cl)Cl.C(Cl)(Cl)Cl>[NH4+:9].[OH-:36].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([S:25]([C:26]4[C:35]5[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][N:34]=5)[N:29]=[CH:28][CH:27]=4)=[O:46])=[CH:23][CH:24]=3)=[N:10][N:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(4-fluorophenyl)-N-(4-(7-methoxy-1,5-naphthyridin-4-ylthio)phenyl)phthalazin-1-amine (29 mg, 0.057 mmol) in CH2Cl2(2 mL) and CHCl3(3 mL) at −78° C. was added mCPBA, 77% (14 mg, 0.080 mmol) in one portion. After 1 hr, the mixture was slowly warmed to 0° C. and stirred for an additional 15 min. The solution was diluted with CH2Cl2 and washed with 10% Na2S2O4 and saturated aqueous NaHCO3. After drying the organic fraction with Na2SO4, the solvent was removed in vacuo and the residue purified by silica gel chromatography using 100% CH2Cl2 to 8% MeOH:CH2Cl2 with 1% NH4OH to afford 4-(4-fluorophenyl)-N-(4-(7-methoxy-1,5-naphthyridin-4-ylsulfinyl)phenyl)phthalazin-1-amine (18 mg, 60% yield) as a light yellow solid. MS: M+H+=522. 1.

Workup

washwashed with 10% Na2S2O4 and saturated aqueous NaHCO3
dry with materialAfter drying the organic fraction with Na2SO4
customthe solvent was removed in vacuo
customthe residue purified by silica gel chromatography

Sources & evidence

ORD record: ord-21fbaa3a35b24217948031c5b565a886
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981891B2

Reaction notes

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