Hydrochloric Acid → HCID 69076182, compound

HRID 225486Notes

Reaction equation

HRID 225486 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[C:11]([N:18]3[CH2:24][CH2:23]C[CH:21](C#N)[CH2:20][CH2:19]3)[C:12]3[S:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[C:4]([F:27])[CH:3]=1.Cl.Cl.CC[O:32][C:33]([CH3:35])=[O:34]>C1COCC1>[ClH:1].[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[C:11]([N:18]3[CH2:19][CH2:20][CH2:21][CH:35]([C:33]([OH:32])=[O:34])[CH2:23][CH2:24]3)[C:12]3[S:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[C:4]([F:27])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21866389Hydrogen chloride-ethyl acetateHCID 66673881HCID 66673881, compound

Product 1

HCID 69076182HCID 69076182, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 260 mg of 1-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]azepane-4-carbonitrile and 35% HCl aq was stirred for 3 hours at 80° C. After the reaction mixture was concentrated and dried under reduced pressure, the obtained residue was purified by silica gel column chromatography (chloroform-MeOH) to give a solid. THF and 0.2 ml of 4M HCl-EtOAc solution were added to the obtained solid. After the solvent was removed under reduced pressure, the residue washed with EtOAc to give 250 mg of 1-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]azepane-4-carboxylic acid hydrochloride.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. customdried under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (chloroform-MeOH)
  4. customto give a solid
  5. customAfter the solvent was removed under reduced pressure
  6. washthe residue washed with EtOAc

Sources & evidence

ORD record
ord-e36782a157c346cc8aff49e8e9b2a5fa
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Reaction notes

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