Benzenesulfonyl chloride → HCID 11752148, compound

HRID 1663136Notes

Reaction equation

HRID 1663136 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][O:5][NH:6][C:7](=[O:22])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.[C:34]1([S:40](Cl)(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>ClCCl>[C:34]1([S:40]([NH:1][C:2]2[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=2[CH2:4][O:5][NH:6][C:7](=[O:22])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][CH2:15][C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 11256552HCID 11256552, compound

Product 1

HCID 11752148HCID 11752148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(2-amino-benzyloxy)-2-[(pyridin-4-ylmethyl)-amino]-benzamide (see example 400) in dichloromethane at 0-5° C. was added triethylamine (1.2 eq.) followed by addition of benzensulfonyl chloride (1.1 eq.). The mixture was allowed to warm to room temperature and stirred for 20 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in EtOAc and washed with water and brine. The organic layer was dried (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc, 2/1, v/v) and gave the title compound. 13C-NMR (DMSO-d6) δ 170.7, 149.6, 149.4, 149.1, 140.7, 138.3, 134.2, 132.5, 131.0, 130.7, 128.8, 127.4, 126.9, 125.3, 124.5, 123.0, 122.2, 115.7, 112.4, 111.1, 76.6, 46.0.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (petroleum ether/EtOAc, 2/1

Sources & evidence

ORD record
ord-4a987c304a08422da0d8f88f9cb8a377
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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