Water → HCID 178518503, compound

HRID 624770Notes

Reaction equation

HRID 624770 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.[CH:50]1([CH2:53][NH2:54])[CH2:52][CH2:51]1.O>CN1C(=O)CCC1.C(Cl)Cl>[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]([NH:54][CH2:53][CH:50]3[CH2:52][CH2:51]3)[N:6]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 75646CyclopropanemethanamineHCID 178504622HCID 178504622, compoundHCID 178504850HCID 178504850, compound

Product 1

HCID 178518503HCID 178518503, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

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 (36 mg) was suspended in NMP (0.2 ml). Cyclopropylmethylamine (88 uL) was added and the mixture stirred at room temperature for 15 minutes. Water and methylene chloride were added and the resulting precipitate was filtered. After triturating in a mixture of ethyl acetate and hexanes, (Z)-5-((4-(cyclopropylamino)-2-(cyclopropylmethylamino)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione was isolated as a yellow solid). LCMS (ES): >95% pure, m/z 355 [M+H]+.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customAfter triturating in a mixture of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-67e994305a3441ad894da13efcb56eae
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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