Triethylamine → HCID 86587126, compound

HRID 2084909Notes

Reaction equation

HRID 2084909 reaction equation
Cl.Cl.[NH2:3][CH:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:11][CH:10]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:23]([O:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)[C:24]#[C:25][CH3:26].C(N(CC)CC)C>ClCCl>[CH2:23]([O:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH:3][CH:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)=[CH:11][CH:10]=2)[C:5]([O:7][CH3:8])=[O:6])(=[O:36])=[O:35])=[CH:30][CH:29]=1)[C:24]#[C:25][CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideHCID 69802348HCID 69802348, compound

Product 1

HCID 86587126HCID 86587126, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° solution of methyl amino{4-[2-(1-pyrrolidinyl)ethoxy]phenyl}acetate dihydrochloride (1.67 g; 4.55 mmol) in dichloromethane (10 mL) was added 4-but-2-ynyloxy-benzenesufonyl chloride followed by triethyl amine was dropped in. The mixture was stirred at room temperature overnight and then diluted with dichloromethane. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified using column chromatography on silica gel eluting with ethyl acetate to obtain 2.52 g of methyl ({[4-(2-butynyloxy)phenyl]sulfonyl}amino){4-[2-(1-pyrrolidinyl)ethoxy]phenyl}acetate as an oil. Yield 92.6%. Electrospray Mass Spec 487.1 (M+H)+.

Workup

  1. additionwas dropped in
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-73023b25846547eb81c268d8ee479ea0
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

Loading…