Tert-Butylamine → HCID 25234371, compound

HRID 2421852Notes

Reaction equation

HRID 2421852 reaction equation
[CH3:1][C:2]1([CH3:25])[S:8][C:7]2[CH:9]=[CH:10][C:11]([C:13](Cl)=[O:14])=[CH:12][C:6]=2[N:5]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:4][CH2:3]1.[C:26]([NH2:30])([CH3:29])([CH3:28])[CH3:27]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:26]([NH:30][C:13]([C:11]1[CH:10]=[CH:9][C:7]2[S:8][C:2]([CH3:25])([CH3:1])[CH2:3][CH2:4][N:5]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C:6]=2[CH:12]=1)=[O:14])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 86628747HCID 86628747, compound

Product 1

HCID 25234371HCID 25234371, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a biphasic mixture of 2,2-dimethyl-5-(phenylsulfonyl)-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepine-7-carbonyl chloride (30 mg, 0.076 mmol) in DCM (2 mL) and saturated aqueous NaHCO3 (2 mL) was added tert-butylamine (25 μL, 0.236 mmol). The reaction was stirred at room temperature for 72 hours. TLC analysis of the reaction mixture indicated consumption of starting material. The biphasic mixture was extracted with DCM (3×2 mL). The combined organics were dried over Na2SO4 and concentrated in vacuo. The resulting solid was purified by flash column chromatography using a gradient elution of Hexanes with 5-50% EtOAc to provide N-tert-butyl-2,2-dimethyl-5-(phenylsulfonyl)-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepine-7-carboxamide (26.3 mg, 0.052 mmol, 68.2% yield) as an off white solid. LCMS (+ESI) m/z=432.9 [M+H]+; 1H-NMR (CDCl3) δ 7.73-7.70 (m, 2H), 7.68-7.63 (m, 2H), 7.55 (tt, 1H), 7.49 (d, 1H), 7.47-7.41 (m, 2H), 5.89 (s, 1H), 3.77 (br s, 1H), 1.88 (br s, 2H), 1.46 (s, 9H), 1.12 (br s, 6H).

Workup

  1. customconsumption of starting material
  2. extractionThe biphasic mixture was extracted with DCM (3×2 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting solid was purified by flash column chromatography
  6. washa gradient elution of Hexanes with 5-50% EtOAc

Sources & evidence

ORD record
ord-4af2f9540a5f49f9aba9a6935e5aa1d7
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

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