Tert-Butylamine → HCID 44242652, compound

HRID 2421893Notes

Reaction equation

HRID 2421893 reaction equation
[N:1]1([S:7]([N:10]2[CH2:15][CH2:14][O:13][C:12]3[N:16]=[CH:17][C:18]([C:20](Cl)=[O:21])=[CH:19][C:11]2=3)(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23]([NH2:27])([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:23]([NH:27][C:20]([C:18]1[CH:17]=[N:16][C:12]2[O:13][CH2:14][CH2:15][N:10]([S:7]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)(=[O:9])=[O:8])[C:11]=2[CH:19]=1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 57896698HCID 57896698, compound

Product 1

HCID 44242652HCID 44242652, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a biphasic mixture of 1-(piperidin-1-ylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonyl chloride (38 mg, 0.110 mmol) in DCM (2 mL) and saturated aqueous NaHCO3 (2 mL) was added tert-butylamine (50 μL, 0.472 mmol). The reaction was stirred at room temperature for 16 h. The biphasic mixture was extracted with DCM (3×2 mL). The combined organics were dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting solid was purified by flash column chromatography using a gradient elution of hexanes with 10-70% EtOAc to provide N-tert-butyl-1-(piperidin-1-ylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxamide (27.7 mg, 0.072 mmol, 65.2% yield over 2 steps) as a white solid. LCMS (+ESI) m/z=383.1 [M+H]+; 1H-NMR (CDCl3) δ 8.27. (d, 1H), 8.17 (d, 1H), 5.86 (br s, 1H), 4.49 (dd, 2H), 3.78 (dd, 2H), 3.29 (dd, 4H), 1.67-1.53 (m, 6H), 1.46 (s, 9H).

Workup

  1. extractionThe biphasic mixture was extracted with DCM (3×2 mL)
  2. dry with materialThe combined organics were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting solid was purified by flash column chromatography
  5. washa gradient elution of hexanes with 10-70% EtOAc

Sources & evidence

ORD record
ord-3df46097e5494f2a90ba96e65c75d744
Source dataset
uspto-grants-2011_06
Patent number
US07960377B2

Reaction notes

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