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Cesium carbonate → [7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(piperazine-1-sulfonyl)-phenyl]-amine HCl salt

HRID 273532
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HRID 273532 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:19]=[C:18]([CH3:20])[C:12]2[N:13]=[C:14]([NH2:17])[N:15]=[N:16][C:11]=2[CH:10]=1.Br[C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]([CH:39]([CH3:41])C)[CH2:32][CH2:33][N:34]2CCCC2)(=[O:30])=[O:29])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:19]=[C:18]([CH3:20])[C:12]2[N:13]=[C:14]([NH:17][C:22]3[CH:23]=[CH:24][C:25]([S:28]([N:31]4[CH2:32][CH2:33][NH:34][CH2:41][CH2:39]4)(=[O:29])=[O:30])=[CH:26][CH:27]=3)[N:15]=[N:16][C:11]=2[CH:10]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 248227577-(2,6-Dichlorophenyl)-5-methylbenzo[e][1,2,4]triazin-3-amineHCID 598377604-bromo-N-isopropyl-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide

생성물 1

HCID 68982670[7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(piperazine-1-sulfonyl)-phenyl]-amine HCl salt

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

실험 절차

In a dry 25 mL round bottom flask, 7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine (0.162 g, 0.533 mmol, 1 equiv), 4-bromo-N-isopropyl-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (0.3 g, 0.8 mmol, 1.5 equiv), cesium carbonate (0.522 g, 1.59 mmol, 3 equiv), 4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene (0.062 g, 0.106 mmol, 0.2 equiv) and tris(dibenzylideneacetone)dipalladium (0.049 g, 0.0533 mmol, 0.1 equiv) were combined. The reactants were flushed with argon, diluted with dioxane (20 mL), and outfitted with a reflux condenser. The reaction was heated to reflux for 2 hours, then filtered hot and the solvents were evaporated. Purification on silica gel flash column provided desired product, 0.144 g yellow solids, which were taken up in 5 mL DCM and treated with 2 mL 2M HCl in ether solution. The solvents were then evaporated and the resulting solids were collected and dried to yield a yellow solid (0.16 g, 50% yield). MS (ESI+): m/z=599.2, LC retention time: 2.99 min. 1H NMR (DMSO-d6): δ 0.98 (d, 6H), 1.88 (m, 2H), 2.01 (m, 2H), 2.72 (s, 3H), 3.02-3.08 (m, 2H), 3.37 (m, 2H), 3.46 (m, 2H), 3.62 (m, 2H), 4.02 (m, 1H), 7.53 (m, 1H), 7.67 (d, J=8.1 Hz, 2H), 7.79 (s, 1H), 7.92 (d, J=8.7 Hz, 2H), 8.18 (d, J=1.6 Hz, 1H), 8.27 (d, J=8.7 Hz, 2H), 10.7 (m, 1H), 11.51 (s, 1H).

후처리

  1. customThe reactants were flushed with argon
  2. additiondiluted with dioxane (20 mL)
  3. customoutfitted with a reflux condenser
  4. temperatureThe reaction was heated
  5. temperatureto reflux for 2 hours
  6. filtrationfiltered hot
  7. customthe solvents were evaporated
  8. customPurification on silica gel flash column

출처 및 근거

ORD 기록
ord-8cf75131bdb14e61b35b1e916608c566
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07456176B2

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