Triethylamine → HCID 22170455, compound

HRID 736382Notes

Reaction equation

HRID 736382 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.[Cl:27][CH2:28][S:29](Cl)(=[O:31])=[O:30].C(N(CC)CC)C>C(Cl)Cl>[Cl:27][CH2:28][S:29]([N:1]([S:29]([CH2:28][Cl:27])(=[O:31])=[O:30])[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:31])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77054(Chloromethyl)sulfonyl chlorideHCID 10382943HCID 10382943, compound

Product 1

HCID 22170455HCID 22170455, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product from Example 3 (500 mg, 1.45 mmol), chloromethanesulfonyl chloride (0.65 g, 4.36 mmol), and triethylamine (1 mL, 7.19 mmol) were stirred in CH2Cl2 (15 mL) overnight at room temperature. The reaction mixture was then diluted with CH2Cl2, washed with H2O and brine, 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, eluant) to provide the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.31 (s, 1H), 8.87 (dd, J=4.7 Hz, 1.3 Hz, 1H), 8.32 (dd, J=8.2 Hz, 1.7 Hz, 1H), 8.14 (d, J=8.5 Hz, 2H), 7.68-7.77 (m, 3H), 7.38 (d, J=8.8 Hz, 2H), 5.46 (s, 1H), 5.42 (s, 1H), 4.97 (s, 1H), 4.92 (s, 1H), 1.29 (s, 9H).

Workup

  1. washwashed with H2O and brine
  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, eluant)

Sources & evidence

ORD record
ord-4da0e3ca9e7f4c58adf261a66902f044
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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