Cesium carbonate → N-(5-{[7-(2-amino-2-oxoethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]carbonyl}pyridin-3-yl)-2-(4-chlorophenyl)acetamide

HRID 82104

Reaction equation

HRID 82104 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([C:18]([C:20]3[C:28]4[CH:27]=[N:26][CH:25]=[N:24][C:23]=4[NH:22][CH:21]=3)=[O:19])[CH:17]=2)=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:36][C:37]([NH2:39])=[O:38]>CN(C=O)C>[NH2:39][C:37](=[O:38])[CH2:36][N:22]1[C:23]2[N:24]=[CH:25][N:26]=[CH:27][C:28]=2[C:20]([C:18]([C:16]2[CH:17]=[C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:13]=[N:14][CH:15]=2)=[O:19])=[CH:21]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 708176452-(4-chlorophenyl)-N-[5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylcarbonyl)pyridin-3-yl]acetamide

Product 1

HCID 70817658N-(5-{[7-(2-amino-2-oxoethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]carbonyl}pyridin-3-yl)-2-(4-chlorophenyl)acetamideYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(4-chlorophenyl)-N-[5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylcarbonyl)pyridin-3-yl]acetamide (Example 308, 50 mg, 0.13 mmol) in DMF (1 ml) was added Cs2CO3 (75 mg, 0.23 mmol) followed by 2-bromoacetamide (21.3 mg, 0.154 mmol). The reaction was then stirred at room temperature overnight. The reaction was quenched with water (5 mL) and extracted with EtOAc (3×5 mL). The organics were combined, washed with water (5 mL) then brine (5 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo. Purification by preparative HPLC gave the title compound in 59% yield, 34 mg.

Workup

  1. customThe reaction was quenched with water (5 mL)
  2. extractionextracted with EtOAc (3×5 mL)
  3. washwashed with water (5 mL)
  4. dry with materialbrine (5 mL), dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-49952a09578e4a01a44231957fd0b892
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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