Acetic Acid → HCID 21043690, compound

HRID 11671Notes

Reaction equation

HRID 11671 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][C:15]([N:17]2[CH2:22][C@H:21]([CH3:23])[N:20]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH2:19][C@H:18]2[CH3:32])=[O:16])=[C:6]([CH2:8][S:9]([NH2:12])(=[O:11])=[O:10])[CH:7]=1.[C:33](O)(=[O:35])[CH3:34].CN(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[C:33]([NH:12][S:9]([CH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:13][CH2:14][C:15]([N:17]1[CH2:22][C@H:21]([CH3:23])[N:20]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[CH2:19][C@H:18]1[CH3:32])=[O:16])(=[O:11])=[O:10])(=[O:35])[CH3:34]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69655403(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-methanesulfonamide

Product 1

HCID 21043690HCID 21043690, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-methanesulfonamide (0.05 g, 0.10 mmol) in dichloromethane (1 mL) was added acetic acid (0.007 g, 0.12 mmol), (3-(dimethylamino)propyl)ethyl carbodiimide (0.030 g, 0.16 mmol), 4-dimethylaminopyridine (0.019 g, 0.16 mmol) and triethylamine (0.023 g, 0.23 mmol). The reaction was stirred at ambient temperature overnight. The reaction was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution and the aqueous layer back extracted with dichloromethane (3×). The organics were combined, dried over sodium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.039 g, LRMS: 526.20).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. extractionthe aqueous layer back extracted with dichloromethane (3×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-807cef5a59614a5391a9b7212767ddf0
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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