Hydrochloric Acid → HCID 54724773, compound

HRID 2216423Notes

Reaction equation

HRID 2216423 reaction equation
[OH:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH:11]([CH3:13])[CH3:12])=[CH:8][CH:9]=2)[S:4][C:3]=1[C:14]([O:16]C)=O.[NH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:27][CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[C:23]([CH:26]=1)[C:24]#[N:25].Cl>>[C:24]([C:23]1[CH:26]=[C:19]([NH:18][C:14]([C:3]2[S:4][C:5]3=[N:6][C:7]([CH:11]([CH3:12])[CH3:13])=[CH:8][CH:9]=[C:10]3[C:2]=2[OH:1])=[O:16])[CH:20]=[CH:21][C:22]=1[O:27][CH2:28][C:29]([CH3:31])([CH3:30])[CH3:32])#[N:25]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 178227345-Amino-2-neopentyloxybenzonitrileHCID 54724774HCID 54724774, compound

Product 1

HCID 54724773HCID 54724773, compoundYield 22.3%

Procedure

Methyl 3-hydroxy-6-isopropylthieno[2,3-b]pyridine-2-carboxylate (1.6 g) and 5-amino-2-neopentyloxybenzonitrile (2.6 g) were stirred at 170° C. for 2 hr. Then the reaction mixture was treated with diluted hydrochloric acid and the organic layer was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained crystals were recrystallized from water-containing dimethylformamide to give the title compound (0.6 g). melting point: 211-212° C.

Workup

  1. extractionthe organic layer was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe obtained crystals were recrystallized from water-
  6. additioncontaining dimethylformamide

Sources & evidence

ORD record
ord-5d00f2f0461a48839d5645515385459e
Source dataset
uspto-grants-2006_09
Patent number
US07112594B2

Reaction notes

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