m-Chloroperbenzoic acid → (1-(5-(1-Methyl-1H-pyrazol-4-yl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(morpholino)methanone

HRID 630485Notes

Reaction equation

HRID 630485 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][C:10]([N:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:22]([N:24]5[CH2:29][CH2:28][O:27][CH2:26][CH2:25]5)=[O:23])[CH:20]=4)[C:15]([S:30][CH3:31])=[CH:14]3)=[N:11][CH:12]=2)[CH:4]=[N:3]1.ClC1C=C(C=CC=1)C(OO)=[O:37].COC1C=CN=C(C2C=NC(N3C4C(=CC=C(C(N5CCOCC5)=O)C=4)C(S(C)=O)=C3)=NC=2)C=1>>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][C:10]([N:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:22]([N:24]5[CH2:25][CH2:26][O:27][CH2:28][CH2:29]5)=[O:23])[CH:20]=4)[C:15]([S:30]([CH3:31])=[O:37])=[CH:14]3)=[N:11][CH:12]=2)[CH:4]=[N:3]1

Participants

4

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 118671977(1-(5-(4-Methoxypyridin-2-yl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(morpholino)methanoneHCID 118676819(1-(5-(1-Methyl-1H-pyrazol-4-yl)pyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone

Product 1

HCID 118666181(1-(5-(1-Methyl-1H-pyrazol-4-yl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(morpholino)methanone

Procedure

The compound obtained in 148a) (380 mg, 0.921 mmol, 1.0 eq) was oxidized with m-chloroperoxybenzoic acid in analogy to the instructions from 141c). White solid. Yield: 150 mg (36% of theory). Melting range: 208-212° C. HPLC (method 6): Rt=7.51 min. Mass spectroscopy: m/z: [M+H]+=451.2.

Sources & evidence

ORD record
ord-bcb06ff360e941839af8eff173ab9db5
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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