Cyclopropanecarbonyl chloride → HCID 178518513, compound

HRID 624723Notes

Reaction equation

HRID 624723 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[N:12]3[N:22]=[CH:23][C:24]([CH:25]=[C:26]4[NH:30][C:29](=[O:31])[NH:28][C:27]4=[O:32])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:21][CH2:20][N:19]([C:36]([CH:33]4[CH2:35][CH2:34]4)=[O:37])[CH2:18][CH2:17]3)[N:12]3[N:22]=[CH:23][C:24]([CH:25]=[C:26]4[NH:30][C:29](=[O:31])[NH:28][C:27]4=[O:32])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 178518511HCID 178518511, compound

Product 1

HCID 178518513HCID 178518513, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-((5-(3-chlorophenylamino)-7-(piperidin-4-ylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (30 mg, 0.066 mmol) in THF was added cyclopropyl carbonyl chloride (5 μL, 0.04 mmol). The mixture was stirred at room temperature for ten minutes. The reaction mixture was then concentrated, diluted with MeOH, and purified by prep HPLC to yield 5-((5-(3-chlorophenylamino)-7-(1-(cyclopropanecarbonyl)piperidin-4-ylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione. LCMS (M+1=521)

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted with MeOH
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-e8444f6007bf48dfb396c4f8a2590b55
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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