Methanesulfonic Acid → HCID 23582499, compound

HRID 1896500Notes

Reaction equation

HRID 1896500 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:14][C:13]3[C:12]([C:15]#[N:16])=[CH:11][N:10]=[C:9]([NH:17]CC4C=CC(OC)=CC=4)[C:8]=3[C:6]=2[CH:7]=1.CS(O)(=O)=[O:29]>>[NH2:17][C:9]1[C:8]2[C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[S:14][C:13]=2[C:12]([C:15]([NH2:16])=[O:29])=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 59198440HCID 59198440, compound

Product 1

HCID 23582499HCID 23582499, compound

Conditions

Temperature
125 °C

Procedure

A suspension of 8-chloro-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile in a 1:1 (mass/mass) mixture of PPA/CH3SO3H (0.8 M) was heated at 125° C. for 2 h. The reaction mixture was cooled to room temperature and partitioned between EtOAc and H2O. The H2O was neutralized with NaHCO3 and NaOH followed by separation of the organic phase. The aqueous phase was extracted again with EtOAc and THF. The solvents were evaporated and the mixture purified by flash chromatography (EtOAc to 10% MeOH in EtOAc) to afford the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between EtOAc and H2O
  3. customfollowed by separation of the organic phase
  4. extractionThe aqueous phase was extracted again with EtOAc and THF
  5. customThe solvents were evaporated
  6. customthe mixture purified by flash chromatography (EtOAc to 10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-6be47b2b4a6441eaa6e04130c9734d21
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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