Triethylamine → HCID 11225739, compound

HRID 1726479Notes

Reaction equation

HRID 1726479 reaction equation
[CH3:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[C:4]([NH:6][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]([S:17](=[O:26])(=[O:25])[NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:9][CH:8]=1)=[O:5].[C:31](Cl)(=[O:35])[CH2:32][CH2:33][CH3:34].C(N(CC)CC)C>C1COCC1>[C:31]([N:22]1[CH2:23][CH2:24][CH:19]([NH:18][S:17]([C:10]2[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:16]=3[C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:27]=[CH:28][CH:29]=[CH:30][C:2]=3[CH3:1])=[CH:8][CH:9]=2)(=[O:26])=[O:25])[CH2:20][CH2:21]1)(=[O:35])[CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 59656440HCID 59656440, compound

Product 1

HCID 11225739HCID 11225739, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 25° C. mixture of sulfonamide (26) (134 mg, 0.29 mmol) in THF (10 mL) was added butyryl chloride (77 mg, 0.725 mmol) and triethylamine (367 mg, 3.625 mmol). The mixture was stirred for 18 hours, followed by filtration to remove the precipitate. The filtrate was concentrated in vacuo and purified via chromatography, resulting in the title compound as white solid (50 mg). 1H NMR (300 MHz, MeOD) δ 7.91 (d, 1H), 7.55 (m, 2H), 7.41 (m, 1H), 7.31 (m, 2H), 4.30 (m, 1H), 3.89 (m, 1H), 3.21 (m, 2H), 3.09 (m, 1H), 2.85 (m, 2H), 2.61 (m, 1H), 2.55 (s, 3H), 2.34 (t, 2H), 1.88 (m, 7H), 1.62 (m, 2H), 1.39 (m, 2H), 0.95 (t, 3H) ); LC/MS (M+H)+ m/z 498.

Workup

  1. filtrationfollowed by filtration
  2. customto remove the precipitate
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified via chromatography

Sources & evidence

ORD record
ord-b8439f90a7fa4b9b9f7109e9b3c463c8
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

Loading…