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Benzylamine → trans-2,2,2-trifluoro-N-[2,3,4,14b-tetrahydro-7-[(phenylmethyl)amino]-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl]acetamide

HRID 16178
ノート
印刷プレビュー

反応式

HRID 16178 の反応式
Br[C:2]1[CH:27]=[CH:26][C:5]2[O:6][C:7]3[CH:25]=[CH:24][CH:23]=[CH:22][C:8]=3[C@@H:9]3[C@H:14]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].[CH2:55]([NH2:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>COCCOC.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]>[F:18][C:17]([F:20])([F:19])[C:16]([NH:15][C@H:14]1[C@@H:9]2[N:10]([C:4]3[CH:3]=[C:2]([NH:62][CH2:55][C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[CH:27]=[CH:26][C:5]=3[O:6][C:7]3[CH:25]=[CH:24][CH:23]=[CH:22][C:8]=32)[CH2:11][CH2:12][CH2:13]1)=[O:21]
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 7504BenzylamineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 86599888trans-N-(7-bromo-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]-oxazepin-1-yl)-2,2,2-trifluoroacetamide

生成物 1

HCID 86599889trans-2,2,2-trifluoro-N-[2,3,4,14b-tetrahydro-7-[(phenylmethyl)amino]-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl]acetamide
収率 32%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
75 °C

実験手順

To a solution of trans-N-(7-bromo-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]-oxazepin-1-yl)-2,2,2-trifluoroacetamide (0.5 g, 1.1 mmol) in DME (16 mL), Pd2(dba)3 (12.5 mg, 13.5 μmol), 2-(di-t-butyl-phosphino)biphenyl (25 mg, 80 μmol), sodium-tert-butoxide (218 mg, 2.3 mmol) and benzylamine (243 mg, 2.3 mmol) were added. The resulting reaction mixture was heated to 75° C. and stirred at this temperature for 48 h. The reaction mixture was quenched with sat NaHCO3 (aq) and extracted with ethyl acetate. The organic layer was washed with water and brine, dried (Na2SO4) and evaporated. The crude product was chromatographed with heptane/ethyl acetate 8:2 and purified with HPLC to afford the title compound (21 mg, 32%). Data: 1H-NMR (400 MHz, DMSO) 1.54-2.02 (m, 4H), 2.95 (t, J=9.2, 1H), 3.68 (d, J=14.0, 1H), 4.02 (d, J=10.0, 1H), 4.17 (d, J=6.0, 2H), 4.37 (m, 1H), 5.90-7.33 (12 ArH, 1 NH), 9.11 (d, J=10.0, 1H). (m/z)=468 (M+H)+.

後処理

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was quenched with sat NaHCO3 (aq)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude product was chromatographed with heptane/ethyl acetate 8:2
  8. custompurified with HPLC

出典と根拠

ORDレコード
ord-acabd88f6b8b48108a0dbcbca4318b9f
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737136B2

反応ノート

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