Methacryloyl chloride → HCID 117703144, compound

HRID 882121Notes

Reaction equation

HRID 882121 reaction equation
[NH2:1][C:2]1[C:3]([F:22])=[C:4]([C:8]2[C:9]3[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:32](Cl)(=[O:36])[C:33]([CH3:35])=[CH2:34]>C1COCC1>[F:22][C:3]1[C:2]([NH:1][C:32](=[O:36])[C:33]([CH3:35])=[CH2:34])=[CH:7][CH:6]=[CH:5][C:4]=1[C:8]1[C:9]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][NH:14][C:10]=2[N:11]=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 13528Methacryloyl chlorideHCID 81531DiisopropylethylamineHCID 117703176HCID 117703176, compound

Product 1

HCID 117703144HCID 117703144, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(3-amino-2-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (6.5 mg, 0.022 mmol) and DIPEA (12 μL, 0.066 mmol) in THF (220 μL) at room temperature was added methacryloyl chloride (3.5 mg, 0.033 mmol) and the solution was stirred for 1 hour. The reaction was concentrated and the residues, dissolved in 2 mL of DMSO, were purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. Lyophilization of the desired fractions afforded a colorless solid. LRMS (ESI) calc'd for C19H18N4O3F [M+H]+: 369, found 369.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residues, dissolved in 2 mL of DMSO
  3. customwere purified by reverse phase HPLC
  4. customLyophilization of the desired fractions afforded a colorless solid

Sources & evidence

ORD record
ord-f3f76b98f1624392b24f044c35fc7bd4
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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