Triethylamine → HCID 22170442, compound

HRID 736375Notes

Reaction equation

HRID 736375 reaction equation
[NH2:1][C:2]1[C:3]([C:8]2[CH:26]=[CH:25][C:11]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=3)=[O:13])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[CH3:34][S:35]([N:1]([S:35]([CH3:34])(=[O:37])=[O:36])[C:2]1[C:3]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH3:22])([CH3:23])[CH3:24])=[CH:17][CH:16]=3)=[O:13])=[CH:25][CH:26]=2)=[N:4][CH:5]=[CH:6][CH:7]=1)(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10382943HCID 10382943, compound

Product 1

HCID 22170442HCID 22170442, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product from Example 3 (300 mg, 0.87 mmol) and triethylamine (0.6 mL, 4.3 mmol) in CH2Cl2 (10 mL) were treated with methanesulfonyl chloride (0.2 mL, 2.58 mmol) at room temperature and stirred overnight. The reaction mixture was diluted with CH2Cl2 (20 mL), washed with H2O (3×5 mL) and brine (5 mL), dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (99:1 CH2Cl2:CH3OH) to provide the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.30 (s, 1H), 8.81 (dd, J=4.6 Hz, 1.6 Hz, 1H), 8.25 (dd, J=8.1 Hz, 1.4 Hz, 1H), 8.11-8.14 (m, 2H), 7.61-7.77 (m, 5H), 7.37-7.41 (m, 2H), 3.19 (s, 6H), 1.29 (s, 9H); MS (ESI+) m/z 502 (M+H)+.

Workup

  1. washwashed with H2O (3×5 mL) and brine (5 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (99:1 CH2Cl2:CH3OH)

Sources & evidence

ORD record
ord-ea5ef5a44df2441faa5679f86fc37286
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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