Hydrochloric Acid → trans-N-(7-Acetyl-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

HRID 16177

반응식

HRID 16177 반응식
[CH2:1]([O:3]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:2].Br[C:20]1[CH:45]=[CH:44][C:23]2[O:24][C:25]3[CH:43]=[CH:42][CH:41]=[CH:40][C:26]=3[C@@H:27]3[C@H:32]([NH:33][C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH2:31][CH2:30][CH2:29][N:28]3[C:22]=2[CH:21]=1.Cl>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([C:20]1[CH:45]=[CH:44][C:23]2[O:24][C:25]3[CH:43]=[CH:42][CH:41]=[CH:40][C:26]=3[C@@H:27]3[C@H:32]([NH:33][C:34](=[O:39])[C:35]([F:36])([F:38])[F:37])[CH2:31][CH2:30][CH2:29][N:28]3[C:22]=2[CH:21]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 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

생성물 1

HCID 86599887trans-N-(7-Acetyl-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide수율 47%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
140 °C

실험 절차

(1-Ethoxyvinyl)tributyl tin (90 μl, 0.23 mmol) was added 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 (100 mg, 0.23 mmol) and PdCl2(PPh3)2 (3 mg, 4.3 μmol) in toluene (6 mL) under N2. The reaction mixture was heated to 140° C. and stirred for 3 h. After cooling to room temperature, 2N (aq) HCl (450 ul) was added and the reaction mixture was stirred for 1 h. The reaction was quenched with sat NaHCO3 (aq) and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and evaporated. The crude compound was chromatographed with heptane/ethyl acetate 1:1. Purifcation by HPLC gave the title compound (43 mg, 47%). Data: 1H-NMR (400 MHz, DMSO) 1.60-2.09 (m, 4H), 3.21 (t, J=11.2, 1H), 3.90 (d, J=14.0, 1H), 4.16 (d, J=10.4, 1H), 4.44 (m, 1H), 7.04-7.54 (m, 10H), 9.20 (d, J=10.0, 1H). (m/z)=405 (M+H)+.

후처리

  1. temperatureAfter cooling to room temperature
  2. stirringthe reaction mixture was stirred for 1 h
  3. customThe reaction was quenched with sat NaHCO3 (aq)
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe crude compound was chromatographed with heptane/ethyl acetate 1:1

출처 및 근거

ORD 기록
ord-f91f3165350549bfa6009c4f389ece63
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737136B2

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