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 633979Notes

Reaction equation

HRID 633979 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, 10 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-bb855893a6684bfcbb62ca6552bd1fde
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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