Hydrochloric Acid → HCID 71014235, compound

HRID 716066Notes

Reaction equation

HRID 716066 reaction equation
[C:1]([C:3]([C:35]([N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)=[O:36])=[CH:4][C:5]1[CH:34]=[CH:33][C:8]([NH:9][C:10]2[N:11]=[C:12]3[C:18]([C:19]([NH:21][CH:22]([CH3:24])[CH3:23])=[O:20])=[CH:17][N:16](COCC[Si](C)(C)C)[C:13]3=[N:14][CH:15]=2)=[CH:7][CH:6]=1)#[N:2].C(O)(C(F)(F)F)=O.Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.CO>[C:1]([C:3]([C:35]([N:37]1[CH2:38][CH2:39][O:40][CH2:41][CH2:42]1)=[O:36])=[CH:4][C:5]1[CH:34]=[CH:33][C:8]([NH:9][C:10]2[N:11]=[C:12]3[C:18]([C:19]([NH:21][CH:22]([CH3:24])[CH3:23])=[O:20])=[CH:17][NH:16][C:13]3=[N:14][CH:15]=2)=[CH:7][CH:6]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 71014225HCID 71014225, compound

Product 1

HCID 71014235HCID 71014235, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a 20 ml vial 2-[4-(2-cyano-3-morpholino-3-oxo-prop-1-enyl)anilino]-N-isopropyl-5-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyrazine-7-carboxamide (65 mg, 0.11 mmol was dissolved in DCM (3 ml) added TFA (3 ml, 0.11 mmol) was added. The reaction mixture was stirred overnight. HCl (1 ml, 0.11 mmol) and methanol (3 ml) were added and the reaction mixture was stirred at overnight and then neutralized to pH 6-7 with NaHCO3. The organics were extracted with EtOAc, washed with water, dried with Na2SO4, filtered and evaporated solvent to give 45 mg of 2-[4-(2-cyano-3-morpholino-3-oxo-prop-1-enyl)anilino]-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide as yellow solid.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at overnight
  3. extractionThe organics were extracted with EtOAc
  4. washwashed with water
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. customevaporated solvent

Sources & evidence

ORD record
ord-d074873df5864ef8b16c8dc9ccb12382
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

Loading…