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 2267488노트

반응식

HRID 2267488 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ec7eb6e510f64a999f7f266b95d0a5e2
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858796B2

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