Triethylamine → HCID 135885187, compound

HRID 2110606Notes

Reaction equation

HRID 2110606 reaction equation
[NH2:1][C:2]1[CH:35]=[CH:34][C:5]2[NH:6][C:7]([C:12]3[C:13](=[O:33])[C:14]([NH:29][C:30](=[O:32])[CH3:31])([CH2:23][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:15]4[C:20]([C:21]=3[OH:22])=[CH:19][CH:18]=[CH:17][CH:16]=4)=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>ClCCl.C(OCC)(=O)C>[CH3:27][C:25]([CH3:28])([CH3:26])[CH2:24][CH2:23][C:14]1([NH:29][C:30](=[O:32])[CH3:31])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]([OH:22])=[C:12]([C:7]2[NH:6][C:5]3[CH:34]=[CH:35][C:2]([NH:1][S:44]([CH3:43])(=[O:46])=[O:45])=[CH:3][C:4]=3[S:9](=[O:10])(=[O:11])[N:8]=2)[C:13]1=[O:33]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 136383512HCID 136383512, compound

Product 1

HCID 135885187HCID 135885187, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of product of Example 74D (1.16 g, 2.33 mmol) in dichloromethane (20 mL) was added triethylamine (1.6 mL, 11.7 mmol) followed by dropwise addition of methanesulfonyl chloride (0.45 mL, 5.84 mmol). The reaction mixture was stirred at room temperature for 18 h. The solution was diluted with ethyl acetate (30 mL), washed with aqueous 1 N HCl (2×15 mL), dried (Na2SO4), and concentrated in vacuo. The resulting residue was taken up in methanol (20 mL) and treated with excess K2CO3 for 2 h. The mixture was filtered. The filtrate was concentrated in vacuo and the resulting residue was taken up in 3:1 dichloromethane:isopropanol (15 mL) and washed with aqueous 1 N HCl (2×10 mL), dried (Na2SO4), and concentrated in vacuo to afford the title compound as a light yellow solid (1.1 g, 82%). 1H NMR (500 MHz, DMSO-d6), δ ppm 0.44-0.54 (m, 1H), 0.66 (s, 9H), 0.87-0.98 (m, 1H), 1.80-1.89 (m, 4H), 1.95-2.05 (m, 1H), 3.08 (s, 3H), 7.53 (t, J=7.25 Hz, 2H), 7.58 (dd, J=8.69, 2.32 Hz, 1H), 7.64 (d, J=2.32 Hz, 1H), 7.70-7.78 (m, 2H), 8.12 (d, J=7.54 Hz, 1H), 9.14 (s, 1H), 10.24 (s, 1H), 13.61 (s, 1H); MS m/z 575.2 (M+H)+.

Workup

  1. washwashed with aqueous 1 N HCl (2×15 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. additiontreated with excess K2CO3 for 2 h
  5. filtrationThe mixture was filtered
  6. concentrationThe filtrate was concentrated in vacuo
  7. washisopropanol (15 mL) and washed with aqueous 1 N HCl (2×10 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0775a1457dbd4f679aa074600f375e9e
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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