Sodium Acetate Trihydrate → {2-[5-(4-hydroxy-piperidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone

HRID 547484Notes

Reaction equation

HRID 547484 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[S:14][C:13]([C:15]3[N:16]=[C:17]4[C:23]([C:24]([C:26]5([CH3:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]5)=[O:25])=[CH:22][N:21](COCC[Si](C)(C)C)[C:18]4=[N:19][CH:20]=3)=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1.O.O.O.C([O-])(=O)C.[Na+]>ClCCl.FC(F)(F)C(O)=O>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([C:10]2[S:14][C:13]([C:15]3[N:16]=[C:17]4[C:23]([C:24]([C:26]5([CH3:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]5)=[O:25])=[CH:22][NH:21][C:18]4=[N:19][CH:20]=3)=[CH:12][CH:11]=2)=[O:9])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 23665404Sodium Acetate TrihydrateHCID 57829606[2-[5-(4-hydroxy-piperidine-1-carbonyl)-thiophen-2-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(1-methyl-cyclohexyl)-methanone

Product 1

HCID 57829623{2-[5-(4-hydroxy-piperidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanoneYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [2-[5-(4-hydroxy-piperidine-1-carbonyl)-thiophen-2-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(1-methyl-cyclohexyl)-methanone (0.032 g, 0.056 mmol) in 1 mL of dichloromethane and 1 mL of trifluoroacetic acid was stirred for 2 h, then concentrated. The residue was dissolved in 2 mL of ethanol and treated with sodium acetate trihydrate (0.076 g, 0.56 mmol). The mixture was stirred overnight, then concentrated to a residue. Column chromatography (0->50% EtOAc/hexanes) afforded 0.019 g (76%) of {2-[5-(4-hydroxy-piperidine-1-carbonyl)-thiophen-2-yl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone as an off-white solid.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 2 mL of ethanol
  3. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-a97439ba37d245e08f8086a52457b3c0
Source dataset
uspto-grants-2011_05
Patent number
US07939531B2

Reaction notes

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