1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-(2-thienyl)-1H-indol-3-yl]-1-piperidinecarboxylate → 3-(4-piperidinyl)-5-(2-thienyl)-1H-indole-7-carboxamide

HRID 2267488ノート

反応式

HRID 2267488 の反応式
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)[CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1)=[O:3]>CO.Cl>[NH:16]1[CH2:17][CH2:18][CH:13]([C:9]2[C:8]3[C:12](=[C:4]([C:2]([NH2:1])=[O:3])[CH:5]=[C:6]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)[CH:7]=3)[NH:11][CH:10]=2)[CH2:14][CH2:15]1

参加物

4

反応物 1

HCID 596006591,1-dimethylethyl 4-[7-(aminocarbonyl)-5-(2-thienyl)-1H-indol-3-yl]-1-piperidinecarboxylate

生成物 1

HCID 596006613-(4-piperidinyl)-5-(2-thienyl)-1H-indole-7-carboxamide収率 77%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒

実験手順

To a solution of 1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-(2-thienyl)-1H-indol-3-yl]-1-piperidinecarboxylate (90 mg, 0.22 mmol) in MeOH (3 mL), HCl (4.0M in dioxane, 2.06 mL) was added. The reaction mixture was stirred at ambient temperature for 2 hours, after which time the solvent was removed under reduced pressure and the resulting residue was partitioned between ethyl acetate (10 mL) and 10% sodium hydroxide (10 mL). The aqueous layer was extracted with ethyl acetate (10 mL×2) and the combined organic phase was dried over MgSO4 and concentrated to give a crude product (53 mg, 77%). This was used directly in the next step without further purification.

後処理

  1. customafter which time the solvent was removed under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate (10 mL) and 10% sodium hydroxide (10 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (10 mL×2)
  4. dry with materialthe combined organic phase was dried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-ec7eb6e510f64a999f7f266b95d0a5e2
出典データセット
uspto-grants-2010_12
特許番号
US07858796B2

反応ノート

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