Potassium Carbonate → HCID 59591441, compound

HRID 1963000Notes

Reaction equation

HRID 1963000 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]#[N:11].C([O-])([O-])=O.[K+].[K+].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.[Cl:34][C:35]1[CH:36]=[CH:37][C:38]2[S:42][C:41]([CH2:43]Cl)=[N:40][C:39]=2[CH:45]=1>CN(C=O)C.O>[Cl:34][C:35]1[CH:36]=[CH:37][C:38]2[S:42][C:41]([CH2:43][O:8][C:7]3[C:2]([F:1])=[C:3]([C:10]#[N:11])[C:4]([F:9])=[CH:5][CH:6]=3)=[N:40][C:39]=2[CH:45]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 1859152-NaphthylalanineHCID 107988395-chloro-2-(chloromethyl)-1,3-benzothiazoleHCID 45119101HCID 45119101, compound

Product 1

HCID 59591441HCID 59591441, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,6-difluoro-3-hydroxybenzenecarbonitrile (4.5 g, 29.0 mmol), K2CO3 (6.01 g, 43.5 mmol) and Nal (0.78 g 5.8 mmol) in DMF (75 ml) was stirred at room temperature for 5 minutes. 5-chloro-2-(chloromethyl)-1,3-benzothiazole was then added and the mixture heated at 40° C. for 18 hours, cooled to room temperature and poured into water (450 ml). Buff solid was filtered off and dried (9.46 g). This was the recrystallised from acetonitrile (30 ml) and dried in vacuo at 40° C. to give a beige solid. Yield 79%, mp 145-147° C., HPLC (Gemini C18, 50×4.6 mm): m/z 337 [M+H]+, Rt=4.93 min.

Workup

  1. temperaturethe mixture heated at 40° C. for 18 hours
  2. temperaturecooled to room temperature
  3. filtrationBuff solid was filtered off
  4. customdried (9.46 g)
  5. customrecrystallised from acetonitrile (30 ml)
  6. customdried in vacuo at 40° C.
  7. customto give a beige solid

Sources & evidence

ORD record
ord-057c172684ac495987a9fc0f6c25c561
Source dataset
uspto-grants-2013_04
Patent number
US08415383B2

Reaction notes

Loading…