Water → HCID 11443666, compound

HRID 902192Notes

Reaction equation

HRID 902192 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[C:14](=[O:25])[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH:22]([CH3:24])[CH3:23])[CH2:18][CH2:17]1)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:33][C:34]([NH:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][N:38]=1)=[O:35].O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:33][C:34](=[O:35])[NH:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][N:38]=1)[N:9]=[C:8]2[C:14](=[O:25])[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH:22]([CH3:23])[CH3:24])[CH2:18][CH2:17]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamideHCID 69033733Methyl 3-[[[1-(1-methylethyl)-4-piperidinyl]amino]carbonyl]-1H-indazole-5-carboxylate

Product 1

HCID 11443666HCID 11443666, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4 g 3-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1H-indazole-5-carboxylic acid methyl ester in 35 mL DMF, 3.8 g Cs2CO3 and 2.9 g 2-Bromo-N-(5-chloro-pyridin-2-yl)-acetamide were added at RT and the reaction mixture was stirred for 2 d. After addition of 50 mL water the mixture was extracted with ethyl acetate (3×150 mL), the combined organic layers were dried over MgSO4 and filtered. The solvents were removed under reduced pressure and the residue was recrystallized from diisopropylether. Yield: 3.8 g MS (ES+): m/e=513, chloro pattern.

Workup

  1. extractionwas extracted with ethyl acetate (3×150 mL)
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customThe solvents were removed under reduced pressure
  5. customthe residue was recrystallized from diisopropylether

Sources & evidence

ORD record
ord-d9561c6e31074d87b552f591b4df2c93
Source dataset
uspto-grants-2008_04
Patent number
US07365088B2

Reaction notes

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