Ethylamine → HCID 59633427, compound

HRID 2369041Notes

Reaction equation

HRID 2369041 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([C:28](O)=[O:29])=[N:9]1.C(N1C=CN=C1)([N:33]1[CH:37]=[CH:36]N=C1)=O.C(N)C.C1COCC1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([C:28]([NH:33][CH2:37][CH3:36])=[O:29])=[N:9]1

Participants

6

Reactant 4

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 59631853HCID 59631853, compound

Product 1

HCID 59633427HCID 59633427, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazole-3-carboxylic acid (92 mg, 0.2 mmol) in DCM (2 mL) was added carbonyldiimidazole (39 mg, 1.2 equiv) and stirring was continued for 2 h at 20° C. A solution of ethylamine in THF (1.8 M, 0.17 mL, 1.5 equiv) was added and the mixture was stirred overnight at 20° C. Evaporation of solvent gave a crude, which was purified by column chromatography on silica gel eluting with MeOH-DCM (1:19) to afford 1-(2-chlorophenyl)-N-ethyl-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazole-3-carboxamide (84 mg). 1H-NMR (CDCl3): δ 8.03 (m, 1H), 7.83 (m, 1H), 7.74 (m, 1H), 7.62-7.45 (m, 5H), 7.22 (m, 1H), 7.19 (s, 1H), 6.91 (m, 1H), 6.82 (d, 1H), 3.55-3.43 (m, 2H), 3.07 (3 s, H), 1.25 (s, 3H). MS(ES): 486 [M+H]+.

Workup

  1. stirringthe mixture was stirred overnight at 20° C
  2. customEvaporation of solvent
  3. customgave a crude, which
  4. customwas purified by column chromatography on silica gel eluting with MeOH-DCM (1:19)

Sources & evidence

ORD record
ord-9b49a963f9174ccb9f92673a42baa5a9
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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