Diethyl Ether → HCID 178484336, compound

HRID 341194Notes

Reaction equation

HRID 341194 reaction equation
[F:1][C:2]([F:27])([F:26])[CH2:3][NH:4][C:5](=[O:25])[NH:6][C:7]1[CH:8]=[C:9]([C:13]2[N:17]3[CH:18]=[CH:19][C:20]([C:22]([NH2:24])=[O:23])=[CH:21][C:16]3=[N:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1.CC(O[CH:33](N(C)C)[N:34]([CH3:36])[CH3:35])(C)C.CCOCC>CN(C=O)C>[CH3:33][N:34]([CH3:36])/[CH:35]=[N:24]/[C:22]([C:20]1[CH:19]=[CH:18][N:17]2[C:13]([C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([NH:6][C:5]([NH:4][CH2:3][C:2]([F:1])([F:26])[F:27])=[O:25])[CH:8]=3)=[CH:14][N:15]=[C:16]2[CH:21]=1)=[O:23]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 25263771HCID 25263771, compound

Product 1

HCID 178484336HCID 178484336, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-[3-[3-(2,2,2-trifluoroethyl)ureido]-phenyl}imidazo[1,2-a]pyridine-7-carboxylic acid amide (20 mg, 0.053 mmol) in dry DMF (0.5 ml) was added Bredereck's reagent (25 μl, 0.12 mmol) and the reaction mixture stirred for 1 h. Et2O was added to the reaction and the resulting precipitate filtered off. The precipitate was redissolved in MeOH, transferred to a flask and the solvent removed in vacuo to afford a pale yellow solid (17 mg). MS: [M+H]+433.

Workup

  1. filtrationthe resulting precipitate filtered off
  2. dissolutionThe precipitate was redissolved in MeOH
  3. customtransferred to a flask
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-764a5b14483240b0a35c4fefde0dfc68
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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