Triethylamine → HCID 22170442, compound

HRID 1822919Notes

Reaction equation

HRID 1822919 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-f9aa1f59e52b44fa98f97aa7a729fa42
Source dataset
uspto-grants-2006_05
Patent number
US07037927B2

Reaction notes

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