Hydrochloric Acid → HCID 59712010, compound

HRID 2222217Notes

Reaction equation

HRID 2222217 reaction equation
[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[C:4]([N:6]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([O:23][CH3:24])[CH:17]=1)[C:7]1[S:8][C:9](C)=[C:10]([C:12](O)=[O:13])[N:11]=1)=[O:5].[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl>ClCCl>[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[C:4]([N:6]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([O:23][CH3:24])[CH:17]=1)[C:7]1[S:8][CH:9]=[C:10]([C:12]([N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:13])[N:11]=1)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 682631,1'-CarbonyldiimidazoleHCID 69286941HCID 69286941, compound

Product 1

HCID 59712010HCID 59712010, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 400 mg (0.85 mmol) 2-[(2,4-dichloro-benzoyl)-(4-chloro-3-methoxy-phenyl)-amino]-5-methyl-thiazole-4-carboxylic acid, 105 μL (1.27 mmol) pyrrolidine and 179 mg (1.10 mmol) 1,1′-carbonyldiimidazole in 12 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 270 mg (60%) of the title compound as colorless solid. MS (m/e): 524.1, 526.1 (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-91e8ac726a234ed0bd13f8a005e28e1e
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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