Acetic Acid → HCID 21963909, compound

HRID 2212362Notes

Reaction equation

HRID 2212362 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=3[F:29])[CH2:16][CH2:15][CH:14]([CH2:17][S:18]([NH2:21])(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:30](O)(=[O:32])[CH3:31].CN(C1C=CC=CN=1)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[C:30]([NH:21][S:18]([CH2:17][CH:14]1[CH2:13][CH2:12][C:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:9])=[O:10])([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])[CH2:16][CH2:15]1)(=[O:20])=[O:19])(=[O:32])[CH3:31]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21963897HCID 21963897, compound

Product 1

HCID 21963909HCID 21963909, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(4-chloro-benzenesulfonyl)-4-(2,5-difluoro-phenyl)-cyclohexyl]-methanesulfonamide (Example 3) (64 mg, 0.14 mmol.), acetic acid (0.011 mL, 0.17 mmol.) and dimethylaminopyridine (20 mg, 0.17 mmol.) in dichloromethane was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (32 mg, 0.17 mmol.) and the mixture stirred at ambient temperature for 18 hours. After dilution with ethyl acetate (25 mL), and washing with 2N aqueous hydrochloric acid (20 mL) and brine (20 mL), drying (MgSO4) and evaporation left a residue which was purified by column chromatography on silica, eluting with ethyl acetate:dichloromethane:iso-hexane (2:1:1), to afford the desired product.

Workup

  1. washAfter dilution with ethyl acetate (25 mL), and washing with 2N aqueous hydrochloric acid (20 mL) and brine (20 mL)
  2. customdrying
  3. custom(MgSO4) and evaporation
  4. waitleft a residue which
  5. customwas purified by column chromatography on silica
  6. washeluting with ethyl acetate:dichloromethane:iso-hexane (2:1:1)

Sources & evidence

ORD record
ord-0ef0436fc5ff4e61a5fb08430826ec77
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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