Pyridine → HCID 57771786, compound

HRID 1174923Notes

Reaction equation

HRID 1174923 reaction equation
C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.[Cl:23][C:24]1[S:25][C:26]2[CH:32]=[C:31]([NH2:33])[CH:30]=[CH:29][C:27]=2[N:28]=1.N1C=CC=CC=1>CN(C=O)C.C(Cl)Cl>[Cl:23][C:24]1[S:25][C:26]2[CH:32]=[C:31]([NH:33][C:20]([C:17]3[CH:16]=[CH:15][C:14]([C:11]4[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=4)=[CH:19][CH:18]=3)=[O:22])[CH:30]=[CH:29][C:27]=2[N:28]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 27826894-(4-Fluorophenyl)benzoic acidHCID 109212032-Chloro-1,3-benzothiazol-6-amine

Product 1

HCID 57771786HCID 57771786, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Add oxalyl chloride (10 mL, 114.6 mmol) and DMF (4 drops) to a stirring suspension of 4′-fluoro-biphenyl-4-carboxylic acid (4.9 g, 22.7 mmol) in CH2Cl2 (150 mL). Stir the reaction mixture at room temperature for 3 h. Concentrate the mixture in vacuo, add n-hexane, re-concentrate, and re-dissolve in CH2Cl2. Add the resultant 4′-fluoro-biphenyl-4-carbonyl chloride solution to a mixture of 2-chloro-benzothiazol-6-ylamine (3.31 g, 17.9 mmol) and pyridine (3.0 mL) in CH2Cl2 (150 mL). Stir the reaction mixture overnight at room temperature. Dilute the reaction mixture with CH2Cl2. Wash the reaction mixture twice with 1.0M HCl and once with 1.0M NaOH. Dry the mixture over Na2SO4, concentrate in vacuo, and triturate with MeOH to yield the desired product (6.34 g, 93%). 1H NMR (400 MHz, DMSO-d6): δ10.59 (s, 1H), 8.69 (d, J=1.6 Hz, 1H), 8.09 (d, J=8.0 Hz, 2H), 7.96 (d, J=8.8 Hz, 1H), 7.87-7.79 (m, 5H), 7.38-7.31 (m, 2H).

Workup

  1. concentrationConcentrate the mixture in vacuo
  2. additionadd n-hexane
  3. concentrationre-concentrate
  4. dissolutionre-dissolve in CH2Cl2
  5. additionAdd the resultant 4′-fluoro-biphenyl-4-carbonyl chloride solution
  6. stirringStir the reaction mixture overnight at room temperature
  7. washWash the reaction mixture twice with 1.0M HCl
  8. dry with materialDry the mixture over Na2SO4
  9. concentrationconcentrate in vacuo
  10. customtriturate with MeOH

Sources & evidence

ORD record
ord-953c6645479b43408bc9cbb75484d5cf
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

Loading…