Sodium Acetate Trihydrate → HCID 57829650, compound

HRID 547487Notes

Reaction equation

HRID 547487 reaction equation
[N:1]1([C:5]([C:7]2[CH:11]=[CH:10][N:9]([C:12]3[N:13]=[C:14]4[C:20]([C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:19][N:18](COCC[Si](C)(C)C)[C:15]4=[N:16][CH:17]=3)[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.O.O.O.C([O-])(=O)C.[Na+]>ClCCl.FC(F)(F)C(O)=O>[N:1]1([C:5]([C:7]2[CH:11]=[CH:10][N:9]([C:12]3[N:13]=[C:14]4[C:20]([C:21](=[O:26])[C:22]([CH3:24])([CH3:23])[CH3:25])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)[CH:8]=2)=[O:6])[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 23665404Sodium Acetate TrihydrateHCID 57829605HCID 57829605, compound

Product 1

HCID 57829650HCID 57829650, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-[2-[3-(azetidine-1-carbonyl)-pyrrol-1-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.066 g, 0.137 mmol) in 2 mL of dichloromethane and 1 mL of trifluoroacetic acid was stirred for 5 h then concentrated. The resulting residue was dissolved in 1 mL of ethanol and treated with sodium acetate trihydrate (0.186 g, 1.37 mmol). The mixture was stirred for 17 h, then concentrated. Column chromatography (1->8% MeOH/CH2Cl2) afforded 0.015 g (31%) of 1-{2-[3-(azetidine-1-carbonyl)-pyrrol-1-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one as a yellow solid.

Workup

  1. concentrationthen concentrated
  2. dissolutionThe resulting residue was dissolved in 1 mL of ethanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-878e387deee645f59e2db0c3fb64d329
Source dataset
uspto-grants-2011_05
Patent number
US07939531B2

Reaction notes

Loading…