1,3-Dichloro-5,5-dimethylhydantoin → 6-Chloro-5-(4-(3-chlorophenoxy)-3-methoxyphenyl)-7-(1-(methylsulfonyl)piperidin-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1615471Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][CH:36]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]([CH:22]3[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]3)[N:15]3[C:20]=2[C:19]([NH2:21])=[N:18][CH:17]=[N:16]3)=[CH:8][C:7]=1[O:32][CH3:33].[Cl:37]N1C(C)(C)C(=O)N(Cl)C1=O>CN(C=O)C>[Cl:37][C:13]1[C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][C:4]3[CH:34]=[CH:35][CH:36]=[C:2]([Cl:1])[CH:3]=3)=[C:7]([O:32][CH3:33])[CH:8]=2)=[C:20]2[N:15]([C:14]=1[CH:22]1[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:29])=[O:30])[CH2:24][CH2:23]1)[N:16]=[CH:17][N:18]=[C:19]2[NH2:21]

Participants

Conditions

Temperature: 65 °C

Procedure

The compound (15.40 mg, 0.029 mmol) prepared in Example 26 and 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (2.87 mg, 0.015 mmol) were taken up in 2 mL of DMF and heated to 65° C. for 16 hours. The reaction was cooled to room temperature and the DMF removed under vacuum and the reaction mixture submitted for prep-HPLC purification to obtain the title compound (12.8 mg) having the following physical data.

Workup

temperatureThe reaction was cooled to room temperature
customthe DMF removed under vacuum
customthe reaction mixture submitted for prep-HPLC purification

Sources & evidence

ORD record: ord-929bf4c8d3b946f8929b40b7276c7062
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765754B2

Reaction notes

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