Tetrahydrofuran → N~2~-{2-Chloro-4-[(4-Methylpiperazin-1-Yl)carbonyl]phenyl}-N~2~,N~8~-Dimethyl-4,5-Dihydrothieno[3,2-D][1]benzoxepine-2,8-Dicarboxamide

HRID 84493

反応式

HRID 84493 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]([N:17]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([N:27]5[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]5)=[O:26])=[CH:21][C:20]=4[Cl:34])[CH3:18])=[O:16])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:35]=1.[N:36]12[CH2:46]CCN=C1CCCC[CH2:37]2.[O:47]1CCCC1>CN.CCOC(C)=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd]>[Cl:34][C:20]1[CH:21]=[C:22]([C:25]([N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)=[O:26])[CH:23]=[CH:24][C:19]=1[N:17]([CH3:18])[C:15]([C:13]1[S:12][C:11]2[C:5]3[CH:4]=[CH:3][C:2]([C:37]([NH:36][CH3:46])=[O:47])=[CH:35][C:6]=3[O:7][CH2:8][CH2:9][C:10]=2[CH:14]=1)=[O:16]

参加物

8

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 568343698-bromo-N-(2-chloro-4-(4-methylpiperazine-1-carbonyl)phenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

生成物 1

HCID 44242776N~2~-{2-Chloro-4-[(4-Methylpiperazin-1-Yl)carbonyl]phenyl}-N~2~,N~8~-Dimethyl-4,5-Dihydrothieno[3,2-D][1]benzoxepine-2,8-Dicarboxamide収率 32%

試薬・触媒・溶媒 4

HCID 98885Molybdenum carbonyl (Mo(CO)6)触媒HCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)触媒HCID 6329Methylamine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

To a solution containing 8-bromo-N-(2-chloro-4-(4-methylpiperazine-1-carbonyl)phenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide (0.075 g, 0.13 mmol) in tetrahydrofuran (1.50 mL, 18.5 mmol), 2.00 M of methylamine in tetrahydrofuran (0.196 mL) was added molybdenumhexacarbonyl (34.4 mg, 0.130 mmol), trans-di(mu-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium (II) (18.3 mg, 0.0196 mmol) then 1,8-diazabicyclo[5.4.0]undec-7-ene (9.75 uL, 0.0652 mmol) and capped quickly to prevent CO gas from escaping. The reaction mixture was heated in a microwave at 150° C. for 20 min. The reaction mixture was diluted with EtOAc then filtered thru celite. The combined organics were dried (Na2SO4), filtered and concentrated. The crude was submitted for RP HPLC to give 181 (yield 32%). MS: (ESI+) 553.2

後処理

  1. filtrationthen filtered thru celite
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-8309b2d57e7d4087b4811b7d5ede439e
出典データセット
uspto-grants-2014_09
特許番号
US08846762B2

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