Water → 4-hydroxy-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide

HRID 1827531Notes

Reaction equation

HRID 1827531 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(OC(=O)[O:34][C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1)C.C(N(CC)CC)C.O>C(Cl)Cl>[OH:34][C:35]1[CH:40]=[CH:39][C:38]([S:41]([N:15]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:14][CH:13]=2)[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)=[CH:19][CH:18]=2)(=[O:43])=[O:42])=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 128842674-(Chlorosulfonyl)phenyl ethyl carbonateHCID 22137309[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amine

Product 1

HCID 221372724-hydroxy-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amine (264 mg, 0.666 mmol) in methylene chloride (10 mL) was treated with carbonic acid 4-chlorosulfonyl-phenyl ester ethyl ester (278 mg, 1.05 mmol) and triethylamine (0.3 mL). The reaction mixture was stirred for 60 hr. and water was added. The aqueous solution was washed with methylene chloride (2×). The combined organic layers were dried (sodium sulfate), filtered, and concentrated in vacuo. The crude product was purified via radial chromatography using a solvent gradient (methylene chloride to 5% methanol/methylene chloride) to obtain the title compound of Step A.

Workup

  1. washThe aqueous solution was washed with methylene chloride (2×)
  2. dry with materialThe combined organic layers were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified via radial chromatography

Sources & evidence

ORD record
ord-cd0ce7e3df6f41a9b2b009264c94b7c8
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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