Water → HCID 22477268, compound

HRID 549022Notes

Reaction equation

HRID 549022 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].[C:24](Cl)(=[O:26])[CH3:25].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][C:24](=[O:26])[CH3:25])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22477209HCID 22477209, compound

Product 1

HCID 22477268HCID 22477268, 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 35] in tetrahydrofuran (1.5 mL) was treated with acetyl chloride (0.0324 mmol) and triethylamine (0.0788 mmol). The solution was stirred at room temperature for 12 hours and then treated with water and ethyl acetate. The organic phase was dried over magnesium sulfate and then evaporated. The residue was subjected to column chromatography on silica eluting with ethyl acetate followed by a mixture of ethyl acetate and methanol (9:1, v/v)) to give the title compound as a yellow solid. MS: 351 (MH+). HPLC (Method C): RT=3.05 minutes.

Workup

  1. dry with materialThe organic phase was dried over magnesium sulfate
  2. customevaporated
  3. additionfollowed by a mixture of ethyl acetate and methanol (9:1

Sources & evidence

ORD record
ord-7063128f9c6d4d069e36278d3679de3f
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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