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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Cesium carbonate → 6-[(6-tert-butylthiomethyl-pyridin-3-ylmethyl)-amino]-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1191118
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HRID 1191118 반응식
[NH2:1][CH2:2][C:3]1[CH:4]=[N:5][C:6]([CH2:9][S:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][CH:8]=1.[Cl:15][C:16]1[CH:32]=[CH:31][C:19]2[CH2:20][CH2:21][N:22]([C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH2:23][CH2:24][C:18]=2[C:17]=1OS(C(F)(F)F)(=O)=O.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(=O)([O-])[O-].[Cs+].[Cs+]>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].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:11]([S:10][CH2:9][C:6]1[N:5]=[CH:4][C:3]([CH2:2][NH:1][C:17]2[C:18]3[CH2:24][CH2:23][N:22]([C:25](=[O:30])[C:26]([F:28])([F:27])[F:29])[CH2:21][CH2:20][C:19]=3[CH:31]=[CH:32][C:16]=2[Cl:15])=[CH:8][CH:7]=1)([CH3:14])([CH3:13])[CH3:12]
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참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 584954543-Aminomethyl-6-(tert-butylthio)methyl-pyridine

생성물 1

HCID 866241646-[(6-tert-butylthiomethyl-pyridin-3-ylmethyl)-amino]-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine
수율 71%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
90 °C

실험 절차

Use a method similar to the General Procedure 1-3. Add 3-aminomethyl-6-(tert-butylthio)methyl-pyridine (2.99 g, 14.2 mmol), 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (5.05 g, 11.9 mmol), tris(dibenzylideneacetone)dipalladium(0) (275 mg, 0.3 mmol), palladium(II) acetate (133 mg, 0.6 mmol), BINAP (560 mg, 0.9 mmol) and cesium carbonate (5.82 g, 17.9 mmol) to toluene (100 mL) under a nitrogen atmosphere. Heat the mixture at 90° C. for 12 h. Cool the mixture to room temperature. Purify by chromatography on silica gel eluting with hexane/EtOAc (100:0 to 85:15 gradient) to obtain 6-[(6-tert-butylthiomethyl-pyridin-3-ylmethyl)-amino]-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (4.1 g, 71%). MS (APCI+) m/z: 486 (M+H)+.

후처리

  1. temperatureCool the mixture to room temperature
  2. customPurify by chromatography on silica gel eluting with hexane/EtOAc (100:0 to 85:15 gradient)

출처 및 근거

ORD 기록
ord-45fc77dbb78646b89ea6e3dc9997c05e
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08680091B2

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