Triethylamine → HCID 69019547, compound

HRID 1865099Notes

Reaction equation

HRID 1865099 reaction equation
C([N:3](CC)CC)C.[CH2:8]([O:10][C:11]([C:13]1[N:14]([CH3:36])[C:15]([CH2:34][CH3:35])=[C:16]([C:32]#[N:33])[C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2N)=[CH:20][CH:19]=1)=[O:12])[CH3:9].[CH:37]([S:40](Cl)(=[O:42])=[O:41])([CH3:39])[CH3:38]>C(Cl)Cl>[CH2:8]([O:10][C:11]([C:13]1[N:14]([CH3:36])[C:15]([CH2:34][CH3:35])=[C:16]([C:32]#[N:33])[C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]([NH:3][S:40]([CH:37]([CH3:39])[CH3:38])(=[O:42])=[O:41])[CH:30]=2)=[CH:20][CH:19]=1)=[O:12])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 57974946HCID 57974946, compound

Product 1

HCID 69019547HCID 69019547, compoundYield 112.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add triethylamine (43 mg, 1.5 Eq.) dropwise to 4-cyano-5-ethyl-1-methyl-3-[4-(2-amino-phenoxy)-phenyl]-1H-pyrole-2-carboxylic acid ethyl ester (110 mg, 0.28 mmol, prepared in example E-231) in methylene chloride (25 mL) while stirring at 0° C. under a nitrogen atmosphere. Immediately add isopropylsulfonyl chloride (48 mg, 1.2Eq.) dropwise and allow the reaction to warm to room temperature and stir overnight. Add water to the mixture and separate layers. Wash the organic layer once with water, dry over potassium carbonate, filter, and concentrate under reduced vacuum to give 156 mg of a solid. Purity the material by silica gel chromatography (Chromatotron™) eluting with methylene chloride/ethyl acetate 19:1 to provide 23 mg of the title compound as a viscous oil. (Bruker 300) 1H NMR (CDCl3) δ 7.30-7.35 (2H, d), 7.22-7.28 (1H, m), 6.99-7.03 (2H, d), 6.89-6.97 (2H, m), 6.75-6.79 (1H, d), 4.06-4.14 (2H, dd), 3.85-3.88 (3H, s), 3.29-3.36 (1H, m), 2.81-2.87 (2H, dd), 1.36-1.42 (6H, d), 1.25-1.32 (3H, t), 1.02-1.09 (3H, t).

Workup

  1. customthe reaction
  2. temperatureto warm to room temperature
  3. stirringstir overnight
  4. customAdd water to the mixture and separate layers
  5. washWash the organic layer once with water
  6. dry with materialdry over potassium carbonate
  7. filtrationfilter
  8. concentrationconcentrate under reduced vacuum

Sources & evidence

ORD record
ord-d82aa3e6b9e94a0282c192b711133870
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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