Cyclopentylamine → HCID 44242731, compound

HRID 2421900Notes

Reaction equation

HRID 2421900 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][O:14][C:13]3[N:17]=[CH:18][C:19]([C:21]4[O:25][N:24]=[C:23]([C:26](Cl)=[O:27])[N:22]=4)=[CH:20][C:12]2=3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH:38]1([NH2:43])[CH2:42][CH2:41][CH2:40][CH2:39]1.C([O-])(O)=O.[Na+]>ClCCCl>[CH:38]1([NH:43][C:26]([C:23]2[N:22]=[C:21]([C:19]3[CH:18]=[N:17][C:13]4[O:14][CH2:15][CH2:16][N:11]([S:8]([C:5]5[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=5)(=[O:10])=[O:9])[C:12]=4[CH:20]=3)[O:25][N:24]=2)=[O:27])[CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 2906CyclopentylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 57896673HCID 57896673, compound

Product 1

HCID 44242731HCID 44242731, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of 5-(1-(4-fluorophenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl)-1,2,4-oxadiazole-3-carbonyl chloride (21 mg, 0.049 mmol) in DCE (5 mL) was added DIPEA (21 μL, 120 μmol) to form a clear solution. To that solution was added cyclopentyl amine (40 μL, 0.099 mmol) and saturated aqueous NaHCO3 (1 mL). The reaction was stirred for 72 hours. LCMS analysis of the reaction mixture indicated consumption of starting material. The reaction 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 to provide N-cyclopentyl-5-(1-(4-fluorophenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl)-1,2,4-oxadiazole-3-carboxamide (7.7 mg, 0.016 mmol, 32.2%) as a white solid. LCMS (+ESI) m/z=474.1 [M+H]+; 1H-NMR (CDCl3) δ 8.90 (d, 1H), 8.87 (d, 1H), 7.75 (m, 2H), 7.21 (m, 2H), 6.97 (m, 1H), 4.47 (m, 1H), 4.09 (dd, 2H), 3.92 (dd, 2H), 2.13 (m, 2H), 1.82-1.52 (m, 6H).

Workup

  1. customto form a clear solution
  2. customconsumption of starting material
  3. extractionThe reaction was extracted with DCM (3×2 mL)
  4. dry with materialThe combined organics were dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was purified by flash column chromatography

Sources & evidence

ORD record
ord-27278073d05f4c5b9f6f1c028275badc
Source dataset
uspto-grants-2011_06
Patent number
US07960377B2

Reaction notes

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