Triethylamine → HCID 87737484, compound

HRID 272735Notes

Reaction equation

HRID 272735 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[C:14]([CH2:17][CH2:18][OH:19])[CH:15]=[CH:16][C:8]=3[NH:7][C:6]=2[CH:20]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>COCCOC.C(OCC)(=O)C>[CH3:28][S:29]([O:19][CH2:18][CH2:17][C:14]1[CH:15]=[CH:16][C:8]2[NH:7][C:6]3[CH:20]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[C:11](=[O:12])[NH:10][C:9]=2[CH:13]=1)(=[O:31])=[O:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69216097HCID 69216097, compound

Product 1

HCID 87737484HCID 87737484, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 204A (1.8 g, 5.58 mmol) in DME (30 mL) was treated with triethylamine (2.33 mL, 16.7 mmol), followed by methanesulfonyl chloride (648 μL, 8.4 mmol) and stirred at ambient temperature for one hour. The reaction mixture was then diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated to give the title compound (2 g, 98% yield). MS (ESI) m/e 367 (M+H)+; 1H NMR (300 MHz, DMSO-d.6 □ 9.89 (s, 1H), 8.03 (s, 1H), 7.68 (d, J=8.5 Hz, 1H). 7.06 (d, J=2.0 Hz, 1H), 6.85-6.94 (m, 4H), 4.33 (t, J=6.6 Hz, 2H), 3.11 (s, 3H), 2.86 (t, J=6.6 Hz, 2H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0f660256311c4bf1bce3f7461095c4bf
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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