Pyridine → HCID 21949214, compound

HRID 2376871Notes

Reaction equation

HRID 2376871 reaction equation
N1C=CC=CC=1.C(N(CC)CC)C.[CH3:14][CH:15]([CH3:38])[CH2:16][CH2:17][NH:18][C:19]([N:21]1[C:29]2[C:24](=[CH:25][C:26]([O:30][C:31]3[CH:36]=[CH:35][N:34]=[C:33]([NH2:37])[CH:32]=3)=[CH:27][CH:28]=2)[CH:23]=[CH:22]1)=[O:20].Cl[C:40]([O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:41]>CN(C)C=O>[CH3:14][CH:15]([CH3:38])[CH2:16][CH2:17][NH:18][C:19]([N:21]1[C:29]2[C:24](=[CH:25][C:26]([O:30][C:31]3[CH:36]=[CH:35][N:34]=[C:33]([NH:37][C:40](=[O:41])[O:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:32]=3)=[CH:27][CH:28]=2)[CH:23]=[CH:22]1)=[O:20]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 21949351HCID 21949351, compound

Product 1

HCID 21949214HCID 21949214, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-dimethylformamide (30 ml), pyridine (0.52 ml, 6.4 mmol) and triethylamine (1.35 ml, 9.69 mmol) were added to N1-(3-methylbutyl)-5-((2-amino-4-pyridyl)oxy)-1H-1-indolecarboxamide (1.45 g, 4.29 mmol); phenyl chloroformate (0.81 ml, 6.4 mmol) was added at 0° C. while stirring; and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was concentrated and subjected to silica gel column chromatography to yield a mixture (2.0 g) of phenyl N-(4-(1-((3-methylbutyl)amino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate and phenyl N-(4-(1-((3-methylbutyl)amino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-N-(phenoxycarbonyl)carbamate. A portion of 0.4 g of the mixture was dissolved in N,N-dimethylformamide (4 ml); 4-(1-pyrrolidinyl)piperidine (0.43 g, 2.8 mmol) was added thereto; and the reaction mixture was stirred for 2 hours. The reaction mixture was partitioned between ethyl acetate and water; the organic layer was concentrated; and the residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate:methanol=10:1) to yield the title compound as white crystals (275 mg, 0.53 mmol).

Workup

  1. stirringand the reaction mixture was stirred at room temperature for 1 hour
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. concentrationand the organic layer was concentrated

Sources & evidence

ORD record
ord-47b5db58184449eea3a0064e76d5855d
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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