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

反応式

HRID 2417001 の反応式
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]

参加物

6

反応物 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

生成物 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)-urea収率 84%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-8219aef5193941dd8d185effa8f46b84
出典データセット
uspto-grants-2004_11
特許番号
US06825184B2

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