Water → HCID 69591925, compound

HRID 1827586Notes

Reaction equation

HRID 1827586 reaction equation
[N:1]1([C:7](=[O:31])[CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1.O>C(Cl)Cl>[CH3:39][O:40][C:41]1[CH:42]=[CH:43][C:44]([S:47]([N:16]([C:13]2[CH:12]=[CH:11][C:10]([CH:9]=[CH:8][C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[O:31])=[CH:15][CH:14]=2)[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)=[CH:20][CH:19]=2)(=[O:49])=[O:48])=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 69591888HCID 69591888, compound

Product 1

HCID 69591925HCID 69591925, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-morpholin-4-yl-3-{4-[4-(tetrahydro-pyran-2-yloxy)benzylamino]-phenyl}-prop-2-en-1-one (0.115 g, 0.27 mmol) and triethylamine (0.100 mL, 0.72 mmol) in 3 mL methylene chloride was added 4-methoxybenzenesulfonyl chloride (0.065 g, 0.31 mmol). The reaction mixture was stirred at room temperature for 60 h. Water was added and the aqueous solution was washed with methylene chloride (3×). The combined organic layers were dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography (50% ethyl acetate/hexanes) gave the title compound of Step B.

Workup

  1. washthe aqueous solution was washed with methylene chloride (3×)
  2. dry with materialThe combined organic layers were dried (magnesium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4c900180bace4db185124a5a700336cd
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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