Pyridine → 5-(2-m-Tolylsulfanylmethybenzoylamino)-1H-pyrazole-3-carboxylic acid methyl ester

HRID 2220737Notes

Reaction equation

HRID 2220737 reaction equation
[NH2:1][C:2]1[N:6](C(OC(C)(C)C)=O)[N:5]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[CH:3]=1.N1C=CC=CC=1.[C:24]1([CH3:41])[CH:29]=[CH:28][CH:27]=[C:26]([S:30][CH2:31][C:32]2[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=2[C:34](Cl)=[O:35])[CH:25]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:17][O:16][C:14]([C:4]1[CH:3]=[C:2]([NH:1][C:34](=[O:35])[C:33]2[CH:37]=[CH:38][CH:39]=[CH:40][C:32]=2[CH2:31][S:30][C:26]2[CH:25]=[C:24]([CH3:41])[CH:29]=[CH:28][CH:27]=2)[NH:6][N:5]=1)=[O:15]

Participants

6

Reactant 3

HCID 1049PyridineHCID 597733355-Amino-1-tert-butoxycarbonyl-3-methoxycarbonylpyrazoleHCID 597735902-m-Tolylthiomethyl-benzoyl chloride

Product 1

HCID 1784984365-(2-m-Tolylsulfanylmethybenzoylamino)-1H-pyrazole-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.1 eq. of 20, 1.1 eq. of pyridine, and 0.07 eq. of DMAP in CH2Cl2 was cooled to 0° C. While stirring, a solution of 1.0 eq. of 59 in CH2Cl2 was added. The reaction solution was allowed to warm to rt. After a time sufficient for reaction completion, the reaction solution was concentrated by rotary evaporation and 1.0 M HCl was added. The acidified solution was extracted with EtOAc. The combined organic extracts were washed with saturated aqueous NaHCO3, followed by drying over MgSO4 and filtering. The filtrate was rotary evaporated and the crude material was purified by flash chromatography on silica gel using a mixture of EtOAc-hexanes as eluant to give 60.

Workup

  1. customAfter a time sufficient for reaction completion
  2. concentrationthe reaction solution was concentrated by rotary evaporation and 1.0 M HCl
  3. additionwas added
  4. extractionThe acidified solution was extracted with EtOAc
  5. washThe combined organic extracts were washed with saturated aqueous NaHCO3
  6. dry with materialby drying over MgSO4
  7. filtrationfiltering
  8. customThe filtrate was rotary evaporated
  9. customthe crude material was purified by flash chromatography on silica gel using
  10. additiona mixture of EtOAc-hexanes as eluant

Sources & evidence

ORD record
ord-0f7593d565474a1397951253c6d5da6e
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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