Methanol → HCID 178518502, compound

HRID 624769Notes

Reaction equation

[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:15]4/[C:16](=[O:21])[NH:17][C:18](=[O:20])[NH:19]/4)=[C:9]3[N:8]=[C:7](S(C)(=O)=O)[N:6]=2)[CH2:3][CH2:2]1.C1(NC2N3N=CC(/C=C4/C(=O)NC(=O)N/4)=C3N=C(S(C)=O)N=2)CC1.[Cl:50][C:51]1[CH:52]=[C:53]([CH:55]=[CH:56][CH:57]=1)[NH2:54].CO>CN1C(=O)CCC1>[Cl:50][C:51]1[CH:52]=[C:53]([NH:54][C:7]2[N:6]=[C:5]([NH:4][CH:1]3[CH2:3][CH2:2]3)[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:15]4/[C:16](=[O:21])[NH:17][C:18](=[O:20])[NH:19]/4)=[C:9]3[N:8]=2)[CH:55]=[CH:56][CH:57]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A (1:1) mixture of (Z)-5-((4-(cyclopropylamino)-2-(methylsulfonyl)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione and (Z)-5-((4-(cyclopropylamino)-2-(methylsulfinyl)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione (15 mg) was mixed with 3-chloroaniline (0.1 ml) in NMP (0.2 ml) and the mixture heated in a microwave oven at 120° C. for 15 min. Methanol was added and the resulting solid filtered and dried to provide (Z)-5-((2-(3-chlorophenylamino)-4-(cyclopropylamino)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione as a solid (7 mg). LCMS (ES): >95% pure, m/z 411 [M+H]+.

Workup

filtrationthe resulting solid filtered
customdried

Sources & evidence

ORD record: ord-996982be474946bd995d42095a1108dd
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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