Succinic anhydride → Succinic acid mono-{1-[2-(3-chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-yl}ester

HRID 1161695Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[C:15]([N:17]3[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]3)[CH:14]=[C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:30]1(=[O:36])[O:35][C:33](=[O:34])[CH2:32][CH2:31]1>CN(C1C=CN=CC=1)C.ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[C:15]([N:17]3[CH2:18][CH2:19][CH:20]([O:23][C:30](=[O:36])[CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH2:21][CH2:22]3)[CH:14]=[C:13]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of compound 1-[2-(3-chloro-4-methoxy-phenylamino)-6-phenyl-pyrimidin-4-yl]-piperidin-4-ol (1.0 g, 2.4 mmol), 4-(N,N-dimethyl)aminopyridine (0.45 g, 3.66 mmol) and succinic anhydride (0.73 g, 7.33 mmol) in dichloroethane (20 mL) was stirred at refluxing temperature for 48 hours. The mixture was cooled to temperature in the range of 20-40° C. and solvent was removed under reduced pressure. The residue was treated with water (20 mL) and the solid precipitated was filtered and washed with isopropanol to give the desired product.

Workup

temperatureat refluxing temperature for 48 hours
customwas removed under reduced pressure
additionThe residue was treated with water (20 mL)
customthe solid precipitated
filtrationwas filtered
washwashed with isopropanol

Sources & evidence

ORD record: ord-5ad261521acf4df8829029f6c5d9ea8e
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820654B2

Reaction notes

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