Perchloric Acid → HCID 25056499, compound

HRID 1690042Notes

Reaction equation

HRID 1690042 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[S:9]1[CH:13]=[CH:12][N:11]=[C:10]1[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O.[CH3:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=1[N+:30]#[C-:31].Cl(O)(=O)(=O)=O>C(O)C>[CH3:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=1[NH:30][C:31]1[N:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]2=[N:1][C:16]=1[C:15]1[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=1[C:10]1[S:9][CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 24247Perchloric AcidHCID 760092,6-Dimethylphenyl isocyanideHCID 27377012-Amino-5-fluoropyridineHCID 155324822-(1,3-Thiazol-2-yl)benzaldehyde

Product 1

HCID 25056499HCID 25056499, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

118 mg (1.0 mmol) of 2-amino-5-fluoropyridine and 189 mg (1.0 mmol) of 2-thiazol-2-ylbenzaldehyde are dissolved successively in 5 ml of ethanol at RT under inert gas. 137 mg (1.0 mmol) of 2,6-dimethyiphenyl isocyanide are then added, 0.043 ml of 70% perchloric acid is added dropwise, and the mixture is stirred at RT for a further 20 h. 10 ml of petroleum ether are subsequently added, and the precipitated solid is filtered off with suction. This is triturated with a little ethyl acetate and filtered off with suction again, giving 177 mg (43%) of (2,6-dimethylphenyl)-[6-fluoro-2-(2-thiazol-2-yl-phenyl)imidazo[1,2-a]pyridin-3-yl]amine (“A1”) as solid; MS-FAB (M+H+)=415.7; Rf (polar method): 1.98 min;

Workup

  1. filtrationthe precipitated solid is filtered off with suction
  2. customThis is triturated with a little ethyl acetate
  3. filtrationfiltered off with suction again

Sources & evidence

ORD record
ord-bbde64bbf19a48bfbc17fb0e33cc3454
Source dataset
uspto-grants-2012_04
Patent number
US08153649B2

Reaction notes

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