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Potassium Carbonate → 3-((3-(5-fluoro-2-(methylamino)-4-pyrimidinyl)-2-pyridinyl)amino)-4-methyl-N-(3-(1-methylethyl)phenyl)benzamide

HRID 446304
ノート
印刷プレビュー

反応式

HRID 446304 の反応式
Cl[C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][N:11]=[C:10]([NH:15][CH3:16])[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:17][C:18]1[CH:19]=[C:20]([CH:33]=[CH:34][C:35]=1[CH3:36])[C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[CH:25]=1)=[O:22].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:14][C:13]1[C:8]([C:7]2[C:2]([NH:17][C:18]3[CH:19]=[C:20]([CH:33]=[CH:34][C:35]=3[CH3:36])[C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[CH:25]=3)=[O:22])=[N:3][CH:4]=[CH:5][CH:6]=2)=[N:9][C:10]([NH:15][CH3:16])=[N:11][CH:12]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 251022283-amino-N-(3-isopropyl-phenyl)-4-methyl-benzamideHCID 86602592[4-(2-Chloro-pyridin-3-yl)-5-fluoro-pyrimidin-2-yl]-methyl-amine

生成物 1

HCID 585882223-((3-(5-fluoro-2-(methylamino)-4-pyrimidinyl)-2-pyridinyl)amino)-4-methyl-N-(3-(1-methylethyl)phenyl)benzamide

試薬・触媒・溶媒

3
HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

[4-(2-Chloro-pyridin-3-yl)-5-fluoro-pyrimidin-2-yl]-methyl-amine (62 mg, 0.26 mmol), 3-amino-N-(3-isopropyl-phenyl)-4-methyl-benzamide (84 mg, 0.31 mmol), Pd(OAc)2 (6 mg, 0.03 mmol), rac-BINAP (16 mg, 0.03 mmol) and K2CO3 (719 mg, 5.2 mmol) in toluene (3.0 mL) were reacted overnight at 130° C. The reaction was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filter, concentrated and purified by reverse-phase HPLC (Gilson, acidic mobile phase) yielding the title compound. MS m/z=471 [M+1]+. Calc'd for C27H27FN6O: 470.55.

後処理

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfilter
  4. concentrationconcentrated
  5. custompurified by reverse-phase HPLC (Gilson, acidic mobile phase)

出典と根拠

ORDレコード
ord-7573af7fd7974e7098b45cf96626be2e
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08476434B2

反応ノート

読み込み中…

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