3-Chlorophenol → HCID 178518505, compound

HRID 2036988Notes

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]([OH:57])[CH:54]=[CH:55][CH:56]=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1.O>[Cl:50][C:51]1[CH:52]=[C:53]([CH:54]=[CH:55][CH:56]=1)[O:57][C:7]1[N:6]=[C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)[N:10]2[N:11]=[CH:12][C:13](/[CH:14]=[C:15]3/[C:16](=[O:21])[NH:17][C:18](=[O:20])[NH:19]/3)=[C:9]2[N:8]=1

Participants

Conditions

Temperature: 90 °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 (1.0 eq, 25 mg, 0.0704 mmol) was combined in a vial with 3-chlorophenol (5.0 eq, 45 mg, 0.35 mmol) and K2CO3 (5.0 eq, 48 mg, 0.347 mmol) in NMP (0.2 ml). The mixture was stirred at 90° C. for 1 hour. Water was added and the resulting solid was filtered and dried. Trituration in a mixture of ethyl acetate and hexanes followed by filtration provided (Z)-5-((2-(3-chlorophenoxy)-4-(cyclopropylamino)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione as a tan solid (20 mg, 69%). LCMS (ES):>95% pure, m/z 412 [M+H]+.

Workup

filtrationthe resulting solid was filtered
customdried
additionTrituration in a mixture of ethyl acetate and hexanes
filtrationfollowed by filtration

Sources & evidence

ORD record: ord-05674ec380c247508183c39121f06f0e
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575177B2

Reaction notes

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