Water → HCID 71286095, compound

HRID 246218Notes

Reaction equation

HRID 246218 reaction equation
[C:1]([CH2:3][CH2:4][C@H:5]([NH:7][C:8]([C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([C:19]3[C:27]4[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=4)[N:21]([CH3:29])[N:20]=3)[N:17]=2)[N:12](COCC[Si](C)(C)C)[CH:11]=1)=[O:9])[CH3:6])#[N:2].C(Cl)Cl.C(N)CN.O>C(O)(C(F)(F)F)=O>[C:1]([CH2:3][CH2:4][C@H:5]([NH:7][C:8]([C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([C:19]3[C:27]4[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=4)[N:21]([CH3:29])[N:20]=3)[N:17]=2)[NH:12][CH:11]=1)=[O:9])[CH3:6])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 6344DichloromethaneHCID 71286077HCID 71286077, compound

Product 1

HCID 71286095HCID 71286095, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(6-Chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-3-cyano-1-methyl-propyl)-amide (120 mg, 0.223 mmol) was dissolved in a 4:6 solution of TFA:DCM (57 mL). After stirring at room temperature overnight, the volatiles were removed under reduced pressure. The crude material was then dissolved in dichloromethane and treated with ethylenediamine (134 mg, 2.23 mmol). After stirring at room temperature overnight, water was added and the resulting precipitate was collected by filtration to provide 45 mg (49%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-3-cyano-1-methyl-propyl)-amide as a yellow solid.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. dissolutionThe crude material was then dissolved in dichloromethane
  3. stirringAfter stirring at room temperature overnight
  4. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-bf6bf1275610446a95e4ba2dce3bfc17
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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