Chloride 2-chloropyridinium 1-oxide → HCID 22598996, compound

HRID 2252469Notes

Reaction equation

HRID 2252469 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[N:5]1.Cl.Cl[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N+:21]=1[O-:26].C(=O)(O)[O-].[Na+]>C(O)CCC>[OH:26][N:21]1[CH:20]=[CH:25][CH:24]=[CH:23][CH:22]1[NH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[N:5]1

Participants

5

Reactant 3

HCID 88478Chloride 2-chloropyridinium 1-oxide2×HCID 516892Sodium Bicarbonate2×HCID 10585718ethyl 1-(2-aminoethyl)-1H-indazole-5-carboxylate

Product 1

HCID 22598996HCID 22598996, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Ethyl 1-(2-aminoethyl)-1H-indazole-5-carboxylate (584 mg, 2.5 mmol, prepared as in step B), was added to dry n-butanol along with 2-chloropyridine-N-oxide hydrochloride (847 mg, 5.1 mmol) and anhydrous sodium bicarbonate (850 mg, 10.1 mmol). The reaction mixture was vigorously stirred and heated at 100 C for 21 hr. Additional aliquots of 2-chloropyridine-N-oxide hydrochloride (847 mg, 5.1 mmol) and anhydrous sodium bicarbonate (850 mg, 10.1 mmol) were added and heating continued for 24 hours. The reaction was cooled and filtered and the filtrate concentrated. The residue was purified by flash chromatography (5% methanol-dichloromethane) and the product fractions concentrated to afford the product as an orange solid (358 mg, 44%). LRMS (ES): 327.1 ([M+H]+, 100%), 653.3 ([2M+H]+, 40%) 1HNMR (600.1343 MHz, CDCl3): 8.44 (s, 1H), 8.12 (s, 1H), 7.97 (d of t, 2H), 7.56 (bs, 1H), 7.45 (d, 1H), 7.06, (m, 1H), 6.45 (m, 1H), 6.35 (t, 1H), 4.68 (t, 2H), 4.37 (q, 2H), 3.90 (q, 2H), 1.39 (t, 3H).

Workup

  1. temperatureheated at 100 C for 21 hr
  2. temperatureheating
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customThe residue was purified by flash chromatography (5% methanol-dichloromethane)
  7. concentrationthe product fractions concentrated

Sources & evidence

ORD record
ord-e0b5e99f1f8444e6a702bc20415976c8
Source dataset
uspto-grants-2008_01
Patent number
US07321045B2

Reaction notes

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