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 273510

반응식

HRID 273510 반응식
[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

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a4fe2dcdc9d84b2e9ed2505d757c5176
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456176B2

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