Water → HCID 12074223, compound

HRID 1369401Notes

Reaction equation

HRID 1369401 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:28](Cl)(=[O:30])[CH3:29].C(N(C(C)C)CC)(C)C.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:28]([NH:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]2)[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:30])[CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 12074222HCID 12074222, compound

Product 1

HCID 12074223HCID 12074223, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl 4-[3-amino-4-(phenylsulfanyl)phenyl]-1-piperazinecarboxylate (0.69 g, 1.6 mmol) in 7 mL of dry CH2Cl2 is cooled to 0° C. Acetyl chloride (0.13 mL, 1.8 mmol), diisopropylethylamine (0.32 mL, 1.8 mmol), and DMAP (0.020 g, 0.16 mmol) are added and the solution allowed to warm to rt overnight with stirring. Water and CH2Cl2 (10 mL each) are added and the layers separated. The aqueous layer is extracted with CH2Cl2 (3×10 mL) and the combined organic layers are washed with 1 N HCl, H2O, and brine. After drying over MgSO4, the mixture is filtered and concentrated to give the crude product. Purification by column chromatography (25% EtOAc/hexane) gives 0.70 g (99%) of the titel compound as a oil.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer is extracted with CH2Cl2 (3×10 mL)
  3. washthe combined organic layers are washed with 1 N HCl, H2O, and brine
  4. dry with materialAfter drying over MgSO4
  5. filtrationthe mixture is filtered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification by column chromatography (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-1a14d3244358446daf2d08652d6977fc
Source dataset
uspto-grants-2003_06
Patent number
US06579870B2

Reaction notes

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