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Binap, (A+-)- → 2-[6-((3R,6R)-5-{[Bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-3,6-dimethyl-6-trifluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-5-fluoro-pyridin-2-ylamino]-nicotinonitrile

HRID 925465
ノート
印刷プレビュー

反応式

HRID 925465 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:24][C:25]2[C@:26]([CH3:44])([C:40]([F:43])([F:42])[F:41])[O:27][CH2:28][C@:29]([C:32]3[C:37]([F:38])=[CH:36][CH:35]=[C:34](Br)[N:33]=3)([CH3:31])[N:30]=2)([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[NH2:45][C:46]1[C:51]([C:52]#[N:53])=[CH:50][CH:49]=[CH:48][N:47]=1.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.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:24][C:25]2[C@:26]([CH3:44])([C:40]([F:43])([F:42])[F:41])[O:27][CH2:28][C@:29]([C:32]3[N:33]=[C:34]([NH:45][C:46]4[N:47]=[CH:48][CH:49]=[CH:50][C:51]=4[C:52]#[N:53])[CH:35]=[CH:36][C:37]=3[F:38])([CH3:31])[N:30]=2)([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 634876Binap, (A+-)-HCID 8182592-Amino-3-cyanopyridineHCID 23676156Sodium t-butoxideHCID 89500352[Bis-(4-methoxy-phenyl)-phenyl-methyl]-[(2R,5R)-5-(6-bromo-3-fluoro-pyridin-2-yl)-2,5-dimethyl-2-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-amine

生成物 1

HCID 90387331
2-[6-((3R,6R)-5-{[Bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-3,6-dimethyl-6-trifluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-5-fluoro-pyridin-2-ylamino]-nicotinonitrile

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of [bis-(4-methoxy-phenyl)-phenyl-methyl]-[(2R,5R)-5-(6-bromo-3-fluoro-pyridin-2-yl)-2,5-dimethyl-2-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-amine (250 mg, 0.372 mmol) in toluene (3.72 ml) was added 2-amino-3-pyridinecarbonitrile (221 mg, 1.859 mmol), Pd2(dba)3 (6.81 mg, 7.43 μmol), BINAP (9.26 mg, 0.015 mmol) and sodium tert-butoxide (50 mg, 0.520 mmol). The reaction mixture was degassed for 5 min and the microwave vial was sealed and stirred at 100° C. for 9 h. The reaction mixture was diluted with DCM and washed with water. The organic layer was dried with Na2SO4. The residue was purified by chromatography (silica gel; eluent DCM/MeOH+NH4OH) to afford the title compound.

後処理

  1. customThe reaction mixture was degassed for 5 min
  2. customthe microwave vial was sealed
  3. additionThe reaction mixture was diluted with DCM
  4. washwashed with water
  5. dry with materialThe organic layer was dried with Na2SO4
  6. customThe residue was purified by chromatography (silica gel; eluent DCM/MeOH+NH4OH)

出典と根拠

ORDレコード
ord-df6dc3d85fc5496fb3e6c86391c95af7
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09284284B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート