Triethylamine → HCID 18625984, compound

HRID 1860091Notes

Reaction equation

HRID 1860091 reaction equation
CS([Cl:5])(=O)=O.C(N(CC)CC)C.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:38]=[CH:37][C:22]([C:23]([NH:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:36]=[CH:35][C:32]([CH2:33]O)=[CH:31][CH:30]=2)=[O:24])=[CH:21][CH:20]=1>ClCCl>[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:38]=[CH:37][C:22]([C:23]([NH:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:36]=[CH:35][C:32]([CH2:33][Cl:5])=[CH:31][CH:30]=2)=[O:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18625863HCID 18625863, compound

Product 1

HCID 18625984HCID 18625984, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (294 mg) and triethylamine (0.37 ml) were successively added to a solution of 4-[3-(4-pyridine-2-ylbenzoylamino)propyl]benzylalcohol (0.74 g) in dichloromethane (20 ml). The mixture was allowed to stand at ambient temperature for 16 hours. The reaction mixture was concentrated. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and concentrated to afford crystals. The crystals were washed with a small amount of diisopropyl ether to afford the desired compound (0.68 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto afford crystals
  8. washThe crystals were washed with a small amount of diisopropyl ether

Sources & evidence

ORD record
ord-ac7ee40b11a04bc29c729cf9caed018c
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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