Triethylamine → HCID 90417145, compound

HRID 633590Notes

Reaction equation

HRID 633590 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][C:6]=1[C:13]1[C:21]2[C:16](=[C:17]([O:22][CH3:23])[N:18]=[CH:19][CH:20]=2)[N:15]([CH3:24])[CH:14]=1.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[S:38](Cl)(=[O:40])=[O:39].C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][S:38]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[O:31][CH3:30])(=[O:40])=[O:39])=[CH:7][C:6]=1[C:13]1[C:21]2[C:16](=[C:17]([O:22][CH3:23])[N:18]=[CH:19][CH:20]=2)[N:15]([CH3:24])[CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 37458512-Methoxybenzenesulfonyl ChlorideHCID 90416939HCID 90416939, compound

Product 1

HCID 90417145HCID 90417145, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 106B (70 mg, 0.177 mmol) in dichloromethane (2.5 mL) was treated with 2-methoxybenzene-1-sulfonyl chloride (43.9 mg, 0.212 mmol) and triethylamine (0.049 mL, 0.354 mmol). The reaction mixture was stirred for 1 hour at ambient temperature and then partitioned between 50% aqueous saturated sodium chloride (50 mL) and ethyl acetate (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to provide the title compound (104 mg, 100% yield).

Workup

  1. custompartitioned between 50% aqueous saturated sodium chloride (50 mL) and ethyl acetate (50 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-064bcd62e82e4f7ab06ae3aee7725b2c
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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