Water → HCID 22477429, compound

HRID 1765584Notes

Reaction equation

HRID 1765584 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:19][C:14]3=[N:15][CH:16]=[CH:17][N:18]=[C:13]3[C:12]=2[CH2:20][CH2:21][CH2:22][NH2:23])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(N(CC)CC)C.O>O1CCCC1.C(OCC)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:19][C:14]3=[N:15][CH:16]=[CH:17][N:18]=[C:13]3[C:12]=2[CH2:20][CH2:21][CH2:22][NH:23][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22477209HCID 22477209, compound

Product 1

HCID 22477429HCID 22477429, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propylamine [0.0324 mmol, Example 24] in tetrahydrofuran (1.5 mL) was treated with methanesulfonyl chloride (0.0324 mmol) and triethylamine (0.0788 mmol). The solution was stirred at room temperature for 12 hours and water and ethyl acetate were added. The layers were separated and the organic solution was dried over magnesium sulfate. The drying agent was filtered and the solvent was evaporated. The residue was purified by column chromatography (silica gel, ethyl acetate followed by 10% methanol in ethyl acetate) to give the title compound as a yellow solid. MS: 387 (MH+). HPLC (Method C): RT=3.23 minutes.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic solution was dried over magnesium sulfate
  3. filtrationThe drying agent was filtered
  4. customthe solvent was evaporated
  5. customThe residue was purified by column chromatography (silica gel, ethyl acetate followed by 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-27ae34a37c0e4d1094ed65a85e1229a7
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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