Hydrochloric Acid → HCID 59712044, compound

HRID 2222216Notes

Reaction equation

HRID 2222216 reaction equation
[Cl:1][C:2]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:3]=1[C:4]([N:6]([C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)[C:7]1[S:8][CH:9]=[C:10]([C:12]([OH:14])=O)[N:11]=1)=[O:5].[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl>ClCCl>[Cl:1][C:2]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:3]=1[C:4]([N:6]([C:7]1[S:8][CH:9]=[C:10]([C:12]([N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:14])[N:11]=1)[C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:24])([F:25])[F:23])=[CH:17][CH:16]=1)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 682631,1'-CarbonyldiimidazoleHCID 69287841HCID 69287841, compound

Product 1

HCID 59712044HCID 59712044, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 250 mg (0.52 mmol) 2-[(2,4-dichloro-benzoyl)-(4-trifluoromethoxy-phenyl)-amino]-thiazole-4-carboxylic acid, 57 μL (0.68 mmol) pyrrolidine and 110 mg (0.68 mmol) 1,1′-carbonyldiimidazole in 10 mL dichloromethane was stirred for 16 h at room temperature. The mixture was poured onto 0.5 N hydrochloric acid and extracted with dichloromethane. Organic phases were pooled, washed with water and brine and dried with MgSO4. Volatiles were removed in vacuo and the residue was purified by silica gel chromatography (n-heptane/ethyl acetate 1:1) to yield 182 mg (65%) of the title compound as colorless solid. MS (m/e): 530.0 (MH+)

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with water and brine
  3. dry with materialdried with MgSO4
  4. customVolatiles were removed in vacuo
  5. customthe residue was purified by silica gel chromatography (n-heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-7296151c236143a8836320dc34b2382b
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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