Tert-Butylamine → HCID 21048969, compound

HRID 2212375Notes

Reaction equation

HRID 2212375 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=3[F:30])[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][S:19](Cl)(=[O:21])=[O:20])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:31]([NH2:35])([CH3:34])([CH3:33])[CH3:32]>ClCCl>[C:31]([NH:35][S:19]([CH2:18][CH2:17][CH:14]1[CH2:15][CH2:16][C:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])[CH2:12][CH2:13]1)(=[O:21])=[O:20])([CH3:34])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 86592995HCID 86592995, compound

Product 1

HCID 21048969HCID 21048969, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(4-chloro-benzenesulfonyl)-4-(2,5-difluoro-phenyl)-cyclohexyl]-ethanesulfonyl chloride (60 mg, 0.12 mmol) (Example 105) in dichloromethane (5 mL) was added tert-butylamine (0.065 mL, 0.62 mmol), the mixture stirred at ambient temperature for 45 minutes, then evaporated. The residue was taken up in ethyl acetate (20 mL) and washed with 2N aqueous hydrochloric acid (20 mL) and brine (100 mL), dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography on silica eluting with diethyl ether:dichloromethane:iso-hexane 1:1:2 to afford the desired product (35 mg). MS (ES+) 556 ([MNa]+).

Workup

  1. customevaporated
  2. washwashed with 2N aqueous hydrochloric acid (20 mL) and brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto leave a residue which
  6. customwas purified by column chromatography on silica eluting with diethyl ether:dichloromethane:iso-hexane 1:1:2

Sources & evidence

ORD record
ord-c37d30d1c8d54c52b180a35af7a507d8
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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