Hydrochloric Acid → HCID 178428795, compound

HRID 548593Notes

Reaction equation

HRID 548593 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([OH:9])[N:6]([CH3:10])[N:5]=2)[CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[C:14]([CH3:21])[C:13]=1[S:22][CH2:23][CH:24]1[CH2:26][CH2:25]1.Cl.CN(C)CCCN=C=NCC.Cl.C(N(CC)CC)C.[C-]#N.[K+]>CC(C)(O)C#N.C(#N)C.C(Cl)Cl>[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([C:8]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[N:5][N:6]([CH3:10])[C:7]=2[OH:9])=[O:17])=[C:14]([CH3:21])[C:13]=1[S:22][CH2:23][CH:24]1[CH2:26][CH2:25]1

Participants

10

Reactant 6

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 671589234-Chloro-3-cyclopropylmethylthio-2-methylbenzoic acidHCID 178481725HCID 178481725, compound

Product 1

HCID 178428795HCID 178428795, compound

Reagents, catalysts & solvents 3

HCID 6406Acetone CyanohydrinCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

161 mg (1.17 mmol) of 3-cyclopropyl-5-hydroxy-1-methylpyrazole and a few drops of N,N-dimethylaminopyridine were added to 272 mg (1.06 mmol) of 4-chloro-3-cyclopropylmethylthio-2-methylbenzoic acid. 244 mg (1.27 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added, and the mixture was stirred at RT for 16 h. For work-up, 3 ml of 1M HCl were added, and the organic phase was freed from the solvent. 214 mg (2.12 mmol) of triethylamine, 10 drops of acetone cyanohydrin and a spatula tip of KCN were added to the residue in 15 ml of acetonitrile. This reaction mixture was stirred at RT for 16 h and then freed from the solvent. 2 ml of 1M HCl were added to the residue in 15 ml of CH2Cl2. The organic phase was freed from the solvent, and the residue was then purified chromatographically. This gave 154 mg of pure product.

Workup

  1. stirringThis reaction mixture was stirred at RT for 16 h
  2. customthe residue was then purified chromatographically

Sources & evidence

ORD record
ord-8320c3a6168446a89366102585cd77a1
Source dataset
uspto-grants-2011_05
Patent number
US07943551B2

Reaction notes

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