N-methyl-2-pyrrolidone → HCID 59432565, compound

HRID 1888913Notes

Reaction equation

HRID 1888913 reaction equation
CCN=C=NCCCN(C)C.[Cl:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:20]1[CH:25]=[C:24]([C:26]2[S:30][CH:29]=[N:28][CH:27]=2)[CH:23]=[C:22]([C:31](O)=[O:32])[CH:21]=1.C1C=[CH:36][C:37]2[N:42](O)N=N[C:38]=2C=1.CN1[C:49](=[O:50])CCC1>C(Cl)Cl.CN(C=O)C>[CH3:49][O:50][CH2:36][CH:37]([NH:42][C:31]([C:22]1[CH:21]=[C:20]([C:14]2[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=2[Cl:12])[CH:25]=[C:24]([C:26]2[S:30][CH:29]=[N:28][CH:27]=2)[CH:23]=1)=[O:32])[CH3:38]

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59432589HCID 59432589, compound

Product 1

HCID 59432565HCID 59432565, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

EDCI (293 mg, 1.53 mmol) was added in one portion to a stirred solution of 2′-Chloro-4′-fluoro-5-thiazol-5-yl-biphenyl-3-carboxylic acid (300 mg, 1.02 mmol), HOBt (207 mg, 1.53 mmol), 2-Amino-1-methoxy-1-propane (1.53 mmol) and NMP (0.5 ml, 4.08 mmol) in CH2Cl2 (5 ml) and DMF (1 ml) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred over night. The reaction mixture was extracted with EtOAc and the combined organic layers were washed with 2N aqueous NaOH, saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give 2′-Chloro-4′-fluoro-5-thiazol-5-yl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (0.347 g, 86%). MS (M+H)=405.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. washthe combined organic layers were washed with 2N aqueous NaOH, saturated aqueous NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7dcfe76fcd2b4677b1a94d2b0b3ced57
Source dataset
uspto-grants-2013_08
Patent number
US08501933B2

Reaction notes

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