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

HRID 1678434ノート

反応式

HRID 1678434 の反応式
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

参加物

9

反応物 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-piperidinecarboxamide2 回

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-aa55639da5b7455fa0b541556a26e5e9
出典データセット
uspto-grants-2011_08
特許番号
US08008483B2

反応ノート

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