Thionyl Chloride → HCID 86710737, compound

HRID 1396565Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:25])[N:9]=[C:10]([C:11]3[C:12]([O:23][CH3:24])=[CH:13][C:14]([O:21][CH3:22])=[C:15]([S:17](O)(=[O:19])=[O:18])[CH:16]=3)[C:5]2=[CH:4][N:3]=1.S(Cl)([Cl:28])=O>>[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:25])[N:9]=[C:10]([C:11]3[C:12]([O:23][CH3:24])=[CH:13][C:14]([O:21][CH3:22])=[C:15]([S:17]([Cl:28])(=[O:19])=[O:18])[CH:16]=3)[C:5]2=[CH:4][N:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 86630407HCID 86630407, compound

Product 1

HCID 86710737HCID 86710737, compound

Conditions

Temperature: 120 °C

Procedure

5-(6-Amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2,4-dimethoxy-benzenesulfonic acid (Example 113) (629 mg, 1.72 mmol) is suspended in thionyl chloride (25 ml), the reaction mixture is heated to 120° C. for 5 hours then stood overnight at room temperature. The resulting precipitate is removed by filtration, the filtrate is concentrated in vacuo and the resulting residue is azeotroped with toluene to afford the title compound as a solid.

Workup

customThe resulting precipitate is removed by filtration
concentrationthe filtrate is concentrated in vacuo
customthe resulting residue is azeotroped with toluene

Sources & evidence

ORD record: ord-164add1a929448969ab7302856ee9f5f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901134B2

Reaction notes

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