Ethylamine → HCID 68655774, compound

HRID 2369060Notes

Reaction equation

HRID 2369060 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]([CH2:28][C:29]([O:31]C)=O)=[N:9]1.[CH2:33]([NH2:35])[CH3:34].Cl.C(N)C>>[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:25])=[O:26])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([CH2:28][C:29]([NH:35][CH2:33][CH3:34])=[O:31])=[N:9]1

Participants

4

Reactant 3

HCID 6341EthylamineHCID 11198Ethylamine hydrochlorideHCID 59632294HCID 59632294, compound

Product 1

HCID 68655774HCID 68655774, compoundYield 83%

Conditions

Temperature
70 °C

Procedure

A mixture of the methyl [1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]acetate (100 mg, 0.2 mmol), EtNH2 (2.0M in THF, 5 mL) and ethylamine hydrochloride (200 mg) was stirred at 70° C. in a sealed vial for 8 h. The solvent was removed in vacuo, another EtNH2/THF (2.0M, 5 mL) was added, the mixture was stirred at 78° C. for another 24 h. Another 3 mL of EtNH2/THF was added, and the mixture was stirred at 78° C. for another 20 h. The solvent was removed in vacuo, and the crude product was purified by flash chromatography (0-30% 20% MeOH/DCM) to give the title compound as a white solid (85 mg, 83%). 1HNMR (CDCl3): δ 8.04 (m, 1H), 7.84-7.82 (m, 1H), 7.74-7.71 (m, 1H), 7.60-7.46 (m, 5H), 7.21 (d, 1H), 6.78 (d, 1H), 6.61 (s, 1H), 6.45 (brs, 1H), 3.69 (s, 2H), 3.30 (q, 2H), 3.07 (s, 3H), 1.14 (t, 3H). MS(ES): 500 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. additionanother EtNH2/THF (2.0M, 5 mL) was added
  3. stirringthe mixture was stirred at 78° C. for another 24 h
  4. additionAnother 3 mL of EtNH2/THF was added
  5. stirringthe mixture was stirred at 78° C. for another 20 h
  6. customThe solvent was removed in vacuo
  7. customthe crude product was purified by flash chromatography (0-30% 20% MeOH/DCM)

Sources & evidence

ORD record
ord-b29ce1d4fbb24c79aba431c0b74d0c3d
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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