Potassium Iodide → HCID 71510766, compound

HRID 1499694Notes

Reaction equation

HRID 1499694 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[Cl:20][C:21]1[C:22]([CH3:44])=[C:23]([C:33]2[CH:34]=[CH:35][C:36]([C:39]([N:41]([CH3:43])[CH3:42])=[O:40])=[N:37][CH:38]=2)[C:24]([O:30][CH2:31][CH3:32])=[C:25]([CH:27](Cl)[CH3:28])[CH:26]=1>CN(C)C=O.O>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([CH:27]([C:25]3[C:24]([O:30][CH2:31][CH3:32])=[C:23]([C:33]4[CH:34]=[CH:35][C:36]([C:39]([N:41]([CH3:42])[CH3:43])=[O:40])=[N:37][CH:38]=4)[C:22]([CH3:44])=[C:21]([Cl:20])[CH:26]=3)[CH3:28])[N:3]=[C:2]([I:1])[C:10]=12

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 86677638HCID 86677638, compoundHCID 178508725HCID 178508725, compound

Product 1

HCID 71510766HCID 71510766, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (from CNH Technologies, 120 mg, 0.46 mmol), cesium carbonate (200 mg, 0.62 mmol) and potassium iodide (7.0 mg, 0.042 mmol) in N,N-dimethylformamide (1 mL) was added 5-[3-chloro-5-(1-chloroethyl)-6-ethoxy-2-methylphenyl]-N,N-dimethylpyridine-2-carboxamide (160 mg, 0.42 mmol, from Example 14, step 4) and the mixture was stirred at 140° C. for 1 hour. The reaction mixture was diluted with water, extracted with ether. The combined organic layers were dried over MgSO4, concentrated and purified on silica gel (eluting with 0 to 10% MeOH in dichloromethane) to give the desired product (0.12 g, 47%). The product was isolated as a racemic mixture. LCMS calculated for C24H26ClIN7O2 (M+H)+: m/z=606.1; Found: 606.0.

Workup

  1. extractionextracted with ether
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated
  4. custompurified on silica gel (eluting with 0 to 10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-96f87e49017c40078583161a901dd548
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

Loading…