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
Reaction equation
[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]1Participants
4
Procedure
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.
Workup
- customafter which time the solvent was removed under reduced pressure
- customthe resulting residue was partitioned between ethyl acetate (10 mL) and 10% sodium hydroxide (10 mL)
- extractionThe aqueous layer was extracted with ethyl acetate (10 mL×2)
- dry with materialthe combined organic phase was dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ec7eb6e510f64a999f7f266b95d0a5e2
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858796B2
Reaction notes
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