Triethylamine → tert-butyl 4-((4-(5-((ethoxycarbonyl)amino)-1H-indol-1-yl)thiazol-2-yl)oxy)piperidine-1-carboxylate

HRID 1468065Notes

Reaction equation

HRID 1468065 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[N:12]=[C:13]([O:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[S:14][CH:15]=1)[CH:6]=[CH:5]2.C(N(CC)CC)C.Cl[CH2:38][CH2:39][O:40][CH:41]=[O:42]>ClCCl>[CH2:39]([O:40][C:41]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[N:12]=[C:13]([O:16][CH:17]3[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]3)[S:14][CH:15]=1)[CH:6]=[CH:5]2)=[O:42])[CH3:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2467482-Chloroethyl formateHCID 67616897tert-Butyl 4-((4-(5-amino-1H-indol-1-yl)thiazol-2-yl)oxy)-piperidine-1-carboxylate

Product 1

HCID 67632626tert-butyl 4-((4-(5-((ethoxycarbonyl)amino)-1H-indol-1-yl)thiazol-2-yl)oxy)piperidine-1-carboxylateYield 9.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-((4-(5-amino-1H-indol-1-yl)thiazol-2-yl)oxy)piperidine-1-carboxylate (intermediate-35) (0.100 g, 0.214 mmol) in dichloromethane (4 mL), triethylamine (0.036 g, 0.362 mmol), and chloroethylformate (0.026 g, 0.214 mmol) were added at 0° C. and stirred at room temperature for 10 minutes. The reaction was quenched with water and the mixture was extracted with dichloromethane. The organic layer was concentrated in vacuo and the residue was purified by flash column chromatography to give tert-butyl 4-((4-(5-((ethoxycarbonyl)amino)-1H-indol-1-yl)thiazol-2-yl)oxy)piperidine-1-carboxylate (0.010 g, 8.5%)

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with dichloromethane
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-babe042881d84ee29386b320832c24a2
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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