Triethylamine → HCID 56926093, compound

HRID 2175460Notes

Reaction equation

HRID 2175460 reaction equation
[CH3:1][C:2]1([CH3:20])[O:19][C:6]2=[N:7][CH:8]=[C:9]([CH2:11][NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=[C:5]2[CH:4]=[CH:3]1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([S:31](Cl)(=[O:33])=[O:32])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][C:2]1([CH3:20])[O:19][C:6]2=[N:7][CH:8]=[C:9]([CH2:11][N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[S:31]([C:25]3[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:23]([O:22][CH3:21])[CH:24]=3)(=[O:33])=[O:32])[CH:10]=[C:5]2[CH:4]=[CH:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 56926092HCID 56926092, compound

Product 1

HCID 56926093HCID 56926093, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 19a (20 mg, 0.075 mmol) in DCM (1 mL) was added 3,4-dimethoxybenzenesulfonyl chloride (36 mg, 0.150 mmol) and triethylamine (0.021 mL, 0.150 mmol). The reaction was stirred for 24 hours at room temperature. The reaction mixture was washed with water (×2) and the organic layer dried over MgSO4 and concentrated in vacuo. Column chromatography (2:1 hexane/EtOAc) gave a white solid (?? g). Yield: 43%. 1H NMR (CDCl3): δ 1.47 (s, 6H), 3.76 (s, 3H), 3.97 (s, 3H), 4.60 (s, 2H), 5.66 (d, 1H, J=9.6), 6.26 (d, 1H, J=10), 6.93-6.99 (m, 4H), 7.23-7.25 (m, 3H), 7.32-7.36 (m, 2H), 7.63 ppm (d, 1H, J=2.4). HRMS (ESI) m/z calcd for C25H25N2O5S [M+H)+] 467.1641. found: 467.1636. HPLC: ret. time=7.5 min, 99.0%

Workup

  1. washThe reaction mixture was washed with water (×2)
  2. dry with materialthe organic layer dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customColumn chromatography (2:1 hexane/EtOAc) gave a white solid (?? g)

Sources & evidence

ORD record
ord-4316f89118e34e0397c4d566cbdcdb73
Source dataset
uspto-grants-2015_06
Patent number
US09062072B2

Reaction notes

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