Triethylamine → HCID 59718028, compound

HRID 2225136Notes

Reaction equation

HRID 2225136 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[CH:10]=[C:9]([S:17](=[O:26])(=[O:25])[NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:8]=1)=[O:5].[C:31](Cl)(=[O:35])[CH:32]([CH3:34])[CH3:33].C(N(CC)CC)C>C1COCC1>[C:31]([N:22]1[CH2:21][CH2:20][CH:19]([NH:18][S:17]([C:9]2[CH:8]=[C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:27]=[CH:28][CH:29]=[CH:30][C:2]=3[CH3:1])[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[CH:10]=2)(=[O:26])=[O:25])[CH2:24][CH2:23]1)(=[O:35])[CH:32]([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 59717977HCID 59717977, compound

Product 1

HCID 59718028HCID 59718028, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 25° C. mixture of sulfonamide (60) (185 mg, 0.4 mmol) in THF (10 mL) was added isobutyryl chloride (107 mg, 1 mmol) and triethyl amine (607 mg, 6 mmol). The mixture was stirred for 18 hours, followed by filtration to remove the solid. The filtrate was concentrated in vacuo and purified via chromatography, to afford the title compound as white solid (17 mg). 1H NMR (300 MHz, MeOD) δ 7.81 (s, 1H), 7.53 (m, 2H), 7.38 (m, 1H), 7.31 (m, 2H), 4.28 (m, 1H), 3.90 (m, 1H), 3.19 (m, 1H), 3.09 (m, 1H), 2.83 (m, 6H), 2.55 (s, 3H), 1.85 (m, 7H), 1.38 (m, 2H), 1.04 (m, 6H) ); LC/MS (M+H)+ m/z 498.

Workup

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

Sources & evidence

ORD record
ord-94f190d8fdba45beb3ddf7c27b8f91ef
Source dataset
uspto-grants-2008_05
Patent number
US07378525B2

Reaction notes

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