2-Aminopyridine → 2-(2-Benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yloxy)-N-pyridin-2-yl-acetamide

HRID 492237Notes

Reaction equation

HRID 492237 reaction equation
[CH2:1]([N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[O:18][CH2:19][C:20](O)=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(O[N:31]1N=N[C:33]2[CH:34]=[CH:35][CH:36]=[N:37][C:32]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.NC1C=CC=CN=1.[Cl-].[NH4+]>C1COCC1>[CH2:1]([N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[O:18][CH2:19][C:20]([NH:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][N:37]=1)=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 104392-AminopyridineHCID 25517Ammonium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10613926(2-Benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yloxy)-acetic acid

Product 1

HCID 166599022-(2-Benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yloxy)-N-pyridin-2-yl-acetamideYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 22 (100 mg, 0.34 mmol) in THF (5 mL) at room temperature was added HATU (141 mg, 0.37 mmol) and TEA (0.07 mL, 0.48 mmol) and the resulting reaction mixture was stirred at room temperature for 10 minutes. Thereafter 2-aminopyridine (35 mg, 0.37 mmol) was added to the reaction mixture and the resulting reaction mixture was allowed to stir at room temperature for 5 hours. The reaction mixture was poured onto saturated ammonium chloride and extracted with ethyl acetate (3×20 mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. Chromatography (SiO2, 20% EtOAc-Hexanes eluant) provided 80 mg of 23 as a clear oil. (126 mg theoretical, 63% yield). 1H NMR (300 MHz, CDCl3): δ 8.85(br s, 1H), 8.35(m, 1H), 8.15(m, 1H), 7.95(m, 1H), 7.7(m, 1H), 7.65-7.45(m, 2H), 7.45(m, 2H), 7.3-7.2(m, 4H), 7.1-7.0(m, 1H), 5.95(s, 1H), 5.05(d, J=15 Hz, 1H), 4.45(d, J=15 Hz, 1H), 3.65(d, J=17 Hz, 1H), 3.45(d, J=17 Hz, 1H). MS (ES) m/z (MH+) 373

Workup

  1. customthe resulting reaction mixture
  2. customthe resulting reaction mixture
  3. stirringto stir at room temperature for 5 hours
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e07d5daa2f6a45cb98f98ea2d1ddd5d5
Source dataset
uspto-grants-2009_05
Patent number
US07531671B2

Reaction notes

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