Methanol → 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(4-pyrrolo[3,2-c]pyridin-1-yl-naphthalen-1-yl)-urea

HRID 2417001

반응식

HRID 2417001 반응식
C1(O[C:8](=[O:26])[NH:9][C:10]2[N:11]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[N:12]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:14]=2)C=CC=CC=1.[NH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([N:38]2[C:46]3[CH:45]=[CH:44][N:43]=[CH:42][C:41]=3[CH:40]=[CH:39]2)=[CH:30][CH:29]=1.CO>CS(C)=O.ClCCl>[C:15]([C:13]1[CH:14]=[C:10]([NH:9][C:8]([NH:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]([N:38]3[C:46]4[CH:45]=[CH:44][N:43]=[CH:42][C:41]=4[CH:40]=[CH:39]3)=[CH:30][CH:29]=2)=[O:26])[N:11]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)[N:12]=1)([CH3:18])([CH3:17])[CH3:16]

참가 물질

6

반응물 3

HCID 887MethanolHCID 11057211phenyl (3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)carbamateHCID 114823371-(4-Aminonaphthalen-1-yl)pyrrolo[3,2-c]pyridine

생성물 1

HCID 101646921-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(4-pyrrolo[3,2-c]pyridin-1-yl-naphthalen-1-yl)-urea수율 84%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

반응 조건

온도
60 °C

실험 절차

(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid phenyl ester (144 mg, 0.411 mmol, 1.1 equiv.) and 1-(4-aminonaphthalen-1-yl)pyrrolo[3,2-c]pyridine (Example 1) (97 mg, 0.374 mmol, 1 equiv.) were combined in 2 mL anhydrous DMSO. The mixture was stirred under inert atmosphere for 1.5 h, then heated to 60° C. for 0.5 h. The reaction was allowed to cool, quenched with 5% aqueous NaOH and extracted with EtOAc three times. The combined organic extracts were washed with water, then brine. They were then dried (MgSO4), filtered, and the solvents were removed in vacuo. The residue was purified by column chromatography using 3-4% MeOH in dichloromethane providing 161 mg title compound (0.313 mmol, 84%) as a glassy solid.

후처리

  1. temperatureto cool
  2. customquenched with 5% aqueous NaOH
  3. extractionextracted with EtOAc three times
  4. washThe combined organic extracts were washed with water
  5. dry with materialThey were then dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvents were removed in vacuo
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-8219aef5193941dd8d185effa8f46b84
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06825184B2

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