1-Methylpiperazine → HCID 59380877, compound

HRID 2354142Notes

Reaction equation

HRID 2354142 reaction equation
C(S[C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11]([C:20]3[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=3)=[N:10][C:8]=2[N:9]=1)C.ClC1C=C(C=CC=1)C(OO)=O.[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>C(Cl)Cl.O1CCOCC1>[CH3:39][N:40]1[CH2:45][CH2:44][N:43]([C:4]2[N:5]=[CH:6][C:7]3[CH:13]=[C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:11]([C:20]4[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=4)=[N:10][C:8]=3[N:9]=2)[CH2:42][CH2:41]1

Participants

6

Reactant 3

HCID 531671-MethylpiperazineHCID 70297m-Chloroperbenzoic acidHCID 860783344-[2-(Ethylthio)-6-phenylpyrido[2,3-d]pyrimidine-7-yl]benzaldehyde

Product 1

HCID 59380877HCID 59380877, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-[2-(ethylthio)-6-phenylpyrido[2,3-d]pyrimidine-7-yl]benzaldehyde (5-4a) (1.0 g, 2.69 mmol) in CH2Cl2 (30 mL) was added m-chloroperoxy benzoic acid (0.660 g, 3.0 mmol). The solution was stirred for 1 hr then quenched with sat. NaHCO3 and 10% Na2S2O3 and stirred for 30 min. The reaction mixture was diluted with CH2Cl2, extracted, dried with MgSO4, and filtered. A portion of the resulting sulfoxide (0.700 g, 1.81 mmol) was dissolved in dioxane (7 mL) with methyl piperazine (181 mg, 1.81 mmol) and heated to 100° C. for 20 min. in a microwave reactor. The mixture was concentrated under reduced pressure and the residue was purified by HPLC (Phenomenx Synergi column; 20-85% acetonitrile/water+0.1% TFA) to give the title compound (5-5a). 1H-NMR (500 MHz, d4-CD3OD) δ 10 (s, 1H), 9.48 (s, 1H), 8.65 (s, 1H), 7.88 (d, 2H), 7.64 (d, 2H), 7.46 (m, 6H), 7.33 (m, 3H), 7.26 (m, 3H), 3.6-3.4 (m, 8H), 3.00 (s, 3H) LRMS m/z (M+1) Calcd: 410.5, found 410.5.

Workup

  1. customthen quenched with sat. NaHCO3 and 10% Na2S2O3
  2. stirringstirred for 30 min
  3. additionThe reaction mixture was diluted with CH2Cl2
  4. extractionextracted
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationThe mixture was concentrated under reduced pressure
  8. customthe residue was purified by HPLC (Phenomenx Synergi column; 20-85% acetonitrile/water+0.1% TFA)

Sources & evidence

ORD record
ord-97d6d4e5a37b4be295b4ed9e16bdca34
Source dataset
uspto-grants-2010_07
Patent number
US07750151B2

Reaction notes

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