Sodium Carbonate → 1-{4-(Methylamino)-6-[4-(methoxy)phenyl]-1,3,5-triazin-2-yl}-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

HRID 1678434노트

반응식

HRID 1678434 반응식
O1[CH2:6][CH2:5][O:4][CH2:3]C1.Cl[C:8]1[N:13]=[C:12]([NH:14][CH3:15])[N:11]=[C:10]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])=[O:23])[CH2:18][CH2:17]2)[N:9]=1.[CH3:36][C:37]1C=CC=[CH:39][C:38]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CC#N>[CH3:15][NH:14][C:12]1[N:13]=[C:8]([C:37]2[CH:36]=[CH:6][C:5]([O:4][CH3:3])=[CH:39][CH:38]=2)[N:9]=[C:10]([N:16]2[CH2:17][CH2:18][CH:19]([C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:33])([F:35])[F:34])=[O:23])[CH2:20][CH2:21]2)[N:11]=1

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27332672-Methylphenyl boronic acidHCID 866443121-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-N-{[-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide2회

생성물 1

HCID 594477541-{4-(Methylamino)-6-[4-(methoxy)phenyl]-1,3,5-triazin-2-yl}-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

In a microwave vial, to a 1,4-dioxane (3.0 ml) suspension of 1-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidine carboxamide (Intermediate 7d, 75 mg, 0.17 mmol, 1.0 equiv) was added (2-methylphenyl)boronic acid (29 mg, 0.21 mmol, 1.2 equiv), Na2CO3 (37 mg, 0.35 mmol, 2.0 equiv) in 3:1 CH3CN:H2O, and lastly Pd(PPh3)4 (10 mg, 0.0088 mmol, 0.05 equiv). The reaction mixture was heated at 150° C. for 25 minutes. The resulting suspension was diluted with ethyl acetate (10 ml), washed with water (5 ml), dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was taken up in 2.0 ml DMSO and purified via reverse-phase HPLC purification to afford the title compound. MS (ES+): m/e 501.0 [M+H]+.

후처리

  1. washwashed with water (5 ml)
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. custompurified via reverse-phase HPLC purification

출처 및 근거

ORD 기록
ord-aa55639da5b7455fa0b541556a26e5e9
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008483B2

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