Dimethylformamide → HCID 21949177, compound

HRID 2215558Notes

Reaction equation

HRID 2215558 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19](=[O:27])OC4C=CC=CC=4)[CH:13]=3)[CH:9]=2)[N:4]([C:28]([NH:30][CH3:31])=[O:29])[CH:3]=1.[CH2:32]([N:34]([CH2:39][CH3:40])[CH2:35][CH2:36][CH2:37][NH2:38])[CH3:33].CN(C)C=O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH3:31][NH:30][C:28]([N:4]1[C:5]2[C:10](=[CH:9][C:8]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]([NH:38][CH2:37][CH2:36][CH2:35][N:34]([CH2:39][CH3:40])[CH2:32][CH3:33])=[O:27])[CH:13]=3)=[CH:7][CH:6]=2)[C:2]([Cl:1])=[CH:3]1)=[O:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 61011N,N-Diethyl-1,3-propanediamineHCID 516892Sodium BicarbonateHCID 21949172HCID 21949172, compound

Product 1

HCID 21949177HCID 21949177, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Phenyl N-(4-(3-chloro-1-(methylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate (160 mg), 3-(diethylamino)propylamine (120 mg), N,N-dimethylformamide (5 ml) were mixed together and stirred at room temperature for 10 minutes. After the addition of aqueous sodium hydrogencarbonate, extraction was performed with ethyl acetate. The purification by silica gel column chromatography (Fuji Silysia NH, ethyl acetate and sequentially ethyl acetate:methanol=10:1) to yield the title compound as a white solid (86 mg).

Workup

  1. customThe purification by silica gel column chromatography (Fuji Silysia NH, ethyl acetate and sequentially ethyl acetate

Sources & evidence

ORD record
ord-933d9286d1b34622b251f3ea9b45f238
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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