Potassium Iodide → HCID 178468211, compound

HRID 624724Notes

Reaction equation

HRID 624724 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.Cl[CH2:34][CH:35]([OH:37])[CH3:36].[I-].[K+]>CN(C=O)C>[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]([CH2:34][CH:35]([OH:37])[CH3:36])[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

5

Reactant 3

HCID 4875Potassium IodideHCID 313701-Chloro-2-propanolHCID 178518511HCID 178518511, compound

Product 1

HCID 178468211HCID 178468211, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

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 DMF was added 1-chloro2-propanol (7 μL, 0.13 mmol) and potassium iodide (11.0 mg, 0.066 mmol). The mixture was heated to 120° C. and stirred for overnight. The reaction mixture was concentrated, diluted with MeOH, and purified by prep HPLC to yield 5-((5-(3-chlorophenylamino)-7-(1-(2-hydroxypropyl)piperidin-4-ylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione. LCMS (M+1=511)

Workup

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

Sources & evidence

ORD record
ord-e76dd13ff51f438f9e80a7f9aac482dc
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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