1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 59224344, compound

HRID 2091553Notes

Reaction equation

HRID 2091553 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:32])=[C:6]([CH:31]=1)[O:7][CH2:8][C:9]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=2[O:26][CH3:27])=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11]([CH3:30])=[CH:12][C:13]([CH3:29])([CH3:28])[NH:14]2.[C:33](N1C=CN=C1)(N1C=CN=C1)=[O:34].[CH3:45][N:46]([CH3:51])[CH2:47][CH2:48][NH:49][CH3:50]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:45][N:46]([CH3:51])[CH2:47][CH2:48][N:49]([C:33]([O:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]2[C:9]([CH2:8][O:7][C:6]3[CH:31]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[CH3:32])=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH3:28])([CH3:29])[CH:12]=[C:11]3[CH3:30])=[C:20]([O:26][CH3:27])[CH:21]=1)=[O:34])[CH3:50]

Participants

6

Reactant 3

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 682631,1'-CarbonyldiimidazoleHCID 16660652HCID 16660652, compound

Product 1

HCID 59224344HCID 59224344, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(5-fluoro-2-methylphenoxymethyl)-6-(4-hydroxy-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 3-1, 26.0 mg, 0.0600 mmol), 1,1′-carbonyldiimidazole (31.4 mg, 0.194 mmol) and 4-dimethylaminopyridine (1.1 mg, 0.0090 mmol) was dissolved in anhydrous tetrahydrofuran (0.6 mL), and then the mixture was stirred at room temperature for 1 hour. N,N,N′-trimethylethylenediamine (15 μL, 0.12 mmol) was added thereto, the mixture was stirred at room temperature for 1 hour, and then the mixture was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (10.0 mg) as a colorless amorphous product. (Yield 30%)

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customthe mixture was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-60b23a6a392c4060a4ce6c4698c0515d
Source dataset
uspto-grants-2013_05
Patent number
US08440660B2

Reaction notes

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