Triethylamine → HCID 11225739, compound

HRID 2225091Notes

Reaction equation

HRID 2225091 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-fba1d0a061a0402cb69e1228820a1b6d
Source dataset
uspto-grants-2008_05
Patent number
US07378525B2

Reaction notes

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