1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 4-[7-(2-chloro-5-nitro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide

HRID 449205

反応式

HRID 449205 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[CH:21]=[C:20]([CH3:22])[C:14]2[N:15]=[C:16]([NH2:19])[N:17]=[N:18][C:13]=2[CH:12]=1.Br[C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:33][CH2:34][CH2:35][N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)(=[O:32])=[O:31])=[CH:26][CH:25]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[K+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[CH:21]=[C:20]([CH3:22])[C:14]2[N:15]=[C:16]([NH:19][C:24]3[CH:29]=[CH:28][C:27]([S:30]([NH:33][CH2:34][CH2:35][N:36]4[CH2:37][CH2:38][CH2:39][CH2:40]4)(=[O:32])=[O:31])=[CH:26][CH:25]=3)[N:17]=[N:18][C:13]=2[CH:12]=1

参加物

7

反応物 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 40330904-Bromo-N-(2-(pyrrolidin-1-yl)ethyl)benzenesulfonamideHCID 23665647Potassium tert-butoxideHCID 598377847-(2-Chloro-5-nitro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine

生成物 1

HCID 598377334-[7-(2-chloro-5-nitro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

7-(2-chloro-5-nitro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine (0.65 mmol, 1.0 equiv), 4-bromo-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (0.95 mmol, 1.5 equiv), Xantphos (0.065 mmol, 0.10 equiv), Pd(OAc)2 (0.033 mmol, 0.05 equiv), and potassium-t-butoxide (1.3 mmol, 2.0 equiv) were dissolved in 45 mL of dioxane and placed under an argon atmosphere. The reaction mixture was refluxed at 100° C. for 18 h and then cooled to room temperature. Inorganic salts were filtered out of solution and the organics were concentrated under reduced pressure. The residue was precipitated using EtOAC/hexanes (1:5 v/v) to afford 4-[7-(2-chloro-5-nitro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide, as a red solid (232 mg, 63% yield). Rf=0.42 MS (ES+) m/z=570. LC retention time 2.56 min.

後処理

  1. temperaturecooled to room temperature
  2. filtrationInorganic salts were filtered out of solution
  3. concentrationthe organics were concentrated under reduced pressure
  4. customThe residue was precipitated

出典と根拠

ORDレコード
ord-4768f35792304862b78a67c781bb8c2c
出典データセット
uspto-grants-2013_07
特許番号
US08481536B2

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