Diisopropylethylamine → HCID 140504872, compound

HRID 2373709Notes

Reaction equation

HRID 2373709 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:23][C:24]([OH:26])=O)=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=2)[S:11][CH:12]=1.Cl.[N:28]1([C:33]([NH2:35])=[NH:34])[CH:32]=[CH:31][CH:30]=[N:29]1.C(N(C(C)C)CC)(C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:23][C:24]([NH:35][C:33](=[NH:34])[N:28]2[CH:32]=[CH:31][CH:30]=[N:29]2)=[O:26])=[C:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[CH:17][CH:18]=2)[S:11][CH:12]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 69198691HCID 69198691, compound

Product 1

HCID 140504872HCID 140504872, compoundYield 54.3%

Procedure

[4-(2-Chlorophenyl)-2-(4-propoxyphenyl)thien-3-yl]acetic acid (0.630 g, 1.62 mmol) was dissolved in CH2CL2 (5 mL) and carbonyldiimidizole (1.31 g, 8.1 mmol) was added. The solution was stirred under argon at room temperature for thirty minutes. 1-H-Pyrazole-1-carboxamidine hydrochloride (2.37 g, 16.2 mmol) and diisopropyl ethylamine (4.23 mL, 3.14 g, 24.3 mmol) were added the solution was stirred overnight. The solvent was removed and the mixture was absorbed onto silica gel and purified by flash chromatography (20:1 CHCl3:MeOH to yield 2-[4-(2-chlorophenyl)-2-(4-propoxyphenyl)thien-3-yl]-N-[imino(1H-pyrazol-1-yl)methyl]acetamide (0.421 g) as a white solid. mp 119-120 ° C.; 1H NMR (500 MHz, DMSO-d6) δ: 0.98 (t, 3H, J=7.3 Hz), 1.73 (m, 2H), 3.55 (s, 2H), 3.96 (t, 2H, J=6.4 Hz), 6.53 (m, 1H), 7.02 (d, 2H, J=8.7 Hz), 7.30 (m, 4H), 7.40 (s, 1H), 7.49 (d, 2H, J=8.5 Hz), 7.89 (s, 1H), 8.08 (s, 1H). MS (ES) m/z 479.1 ([M+H]+). MS (ES) m/z 957.2 ([2M+H]+). MS (ES) m/z 979.2 ([2M+NA]+). Anal. Calcd for C25H23ClN4O2S: C, 62.69; H, 4.84; N, 11.70. Found: C, 62.35; H, 4.86; N, 11.58.

Workup

  1. additionwas added
  2. stirringwas stirred overnight
  3. customThe solvent was removed
  4. customthe mixture was absorbed onto silica gel
  5. custompurified by flash chromatography (20:1 CHCl3

Sources & evidence

ORD record
ord-e51fbb59bd5b42d4bfe6f424ebcfd70e
Source dataset
uspto-grants-2008_12
Patent number
US07459567B2

Reaction notes

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