Pyridine → HCID 58692198, compound

HRID 2264269Notes

Reaction equation

HRID 2264269 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([N:16]3[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]3)[N:11]=2)=[CH:2]1.[C:23](OC(=O)C)(=[O:25])[CH3:24].N1C=CC=CC=1.C1COCC1>O>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([N:16]3[CH2:17][CH2:18][CH:19]([NH:22][C:23](=[O:25])[CH3:24])[CH2:20][CH2:21]3)[N:11]=2)=[CH:2]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 56673427HCID 56673427, compound

Product 1

HCID 58692198HCID 58692198, compoundYield 661.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask was added compound 62 (10.2 mg), acetic anhydride (0.5 mg), pyridine (0.1 mL) and THF (1 mL) at 0° C. The mixture was warmed to rt slowly and stirred for 1 hr, then poured into water and extracted with EtOAc. The organic layer was separated, dried with MgSO4, then concentrated to provide 10.9 mg (94%) of the desired product as a white solid. 1H NMR (400 MHz, DMSO) δ 12.30 (s, 1 H), 8.70 (d, 1 H), 8.40 (s, 1 H), 8.25 (m, 1 H), 8.20 (d, 1 H), 7.80 (d, 1 H), 7.25 (m, 1 H), 7.10 (d, 1 H), 4.60 (d, 2 H), 3.90 (m, 1 H), 3.15 (m, 2 H), 1.85 (m, 2 H), 1:80 (s, 3 H), 1.40 (m, 2 H). MS (ESI) m/z: 337 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ad6dac390ad04af79847f40116a55623
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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