Dichloromethane → (E)-3-(3-(2-(4-Methylpiperazin-1-yl)ethyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-6-yl)acrylic acid hydrochloride

HRID 83025Notes

Reaction equation

HRID 83025 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[CH2:22][C:21]3[CH:23]=[C:24](/[CH:27]=[CH:28]/[C:29]([O:31]C(C)(C)C)=[O:30])[CH:25]=[N:26][C:20]=3[NH:19][C:18]2=[O:36])[CH2:11][CH2:10]1.[Cl:37]CCl>>[ClH:37].[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[CH2:22][C:21]3[CH:23]=[C:24](/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30])[CH:25]=[N:26][C:20]=3[NH:19][C:18]2=[O:36])[CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68338119(E)-tert-Butyl 3-(3-(2-(4-methylpiperazin-1-yl)ethyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-6-yl)acrylate

Product 1

HCID 70927051(E)-3-(3-(2-(4-Methylpiperazin-1-yl)ethyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-6-yl)acrylic acid hydrochloride

Procedure

Trifluoroacetic acid (2 mL) was added to a suspension (E)-tert-butyl 3-(3-(2-(4-methylpiperazin-1-yl)ethyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-6-yl)acrylate (1.1 g, 3.76 mmol) in dichloromethane (2 mL). The reaction mixture was stirred at room temperature for 1 hour and concentrated to dryness. The resulting residue was solubilized in a solution of hydrochloric acid in dioxane (4N, mL). After 10 minutes stirring at room temperature, the precipitate was filtered and washed with diethyl ether to afford the title product as a pale yellow solid (90 mg, quantitative).

Workup

  1. concentrationconcentrated to dryness
  2. stirringAfter 10 minutes stirring at room temperature
  3. filtrationthe precipitate was filtered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-8693803d12ba4f29a2729bf9c9413513
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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