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Triethylamine → N-((4-(Dibenzo[b,f][1,4]thiazepin-11-yl)-1-(2-(2-hydroxyethoxy)ethyl)piperazin-2-yl)methyl)-2,2,2-trifluoroacetamide

HRID 625177
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HRID 625177 반응식
Cl[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=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.C(N(CC)CC)C.[F:70][C:71]([F:89])([F:88])[C:72]([NH:74][CH2:75][CH:76]1[CH2:81][NH:80][CH2:79][CH2:78][N:77]1[CH2:82][CH2:83][O:84][CH2:85][CH2:86][OH:87])=[O:73]>O1CCOCC1.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]>[CH:9]1[C:8]2[C:2]([N:80]3[CH2:79][CH2:78][N:77]([CH2:82][CH2:83][O:84][CH2:85][CH2:86][OH:87])[CH:76]([CH2:75][NH:74][C:72](=[O:73])[C:71]([F:89])([F:88])[F:70])[CH2:81]3)=[N:3][C:4]3[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=3[S:6][C:7]=2[CH:12]=[CH:11][CH:10]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 634876Binap, (A+-)-HCID 1058648111-Chlorodibenzo(b,f)(1,4)thiazepineHCID 867111502,2,2-Trifluoro-N-((1-(2-(2-hydroxyethoxy)ethyl)piperazin-2-yl)methyl)acetamide

생성물 1

HCID 86711152N-((4-(Dibenzo[b,f][1,4]thiazepin-11-yl)-1-(2-(2-hydroxyethoxy)ethyl)piperazin-2-yl)methyl)-2,2,2-trifluoroacetamide

시약·촉매·용매

2
HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 11-chlorodibenzo[b,f][1,4]thiazepine, prepared as described in the previous step, (2 g, crude) in dioxane (20 mL) was added Pd2(dba)3 (327 mg, 0.357 mmol), BINAP (225 mg, 0.357 mmol), triethylamine (6 mL, 42.9 mmol) and 2,2,2-trifluoro-N-((1-(2-(2-hydroxyethoxy)ethyl)piperazin-2-yl)methyl)acetamide, prepared as described as Step F, (2.4 g, crude). The resulting mixture was heated to reflux overnight under nitrogen atmosphere, filtered through CELITE™, and concentrated. The residue was purified by silica gel chromatography to provide the title compound. ESI-MS (M+1): 509 calc. for C24H27F3N4O3S 508.

후처리

  1. customprepared
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux overnight under nitrogen atmosphere
  4. filtrationfiltered through CELITE™
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-113f5628de674dd183634be2cd94789b
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09304126B2

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