Pyridine → HCID 68864047, compound

HRID 1725892Notes

Reaction equation

HRID 1725892 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13].[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](Cl)(=[O:24])=[O:23].N1C=CC=CC=1>ClCCl>[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([NH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 68862599HCID 68862599, compound

Product 1

HCID 68864047HCID 68864047, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 2-amino-1-naphthoate (85 mg, 0.42 mmol) and 2-pyridinesulfonyl chloride (244 mg, 1.3 mmol) in dichloromethane (1.0 mL) was treated with pyridine (0.15 mL, 1.3 mmol), stirred for 15 minutes, treated with dichloromethane (30 mL), washed with 1N HCl (2×20 mL), and concentrated. The crude product was chromatographed on a silica gel column eluting with 30% ethyl acetate/hexanes to provide the desired product (120 mg, 83.5%). 1H NMR (CDCl3) δ 4.09 (s, 3H), 7.35-7.55 (m, 3H), 7.75-7.96 (m, 5H), 8.16 (d, 1H), 8.59 (d, 1H), 9.46 (s, 1H); MS (DCI/NH3) m/e 343 (M+H)+.

Workup

  1. washwashed with 1N HCl (2×20 mL)
  2. concentrationconcentrated
  3. customThe crude product was chromatographed on a silica gel column
  4. washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fed470ebd491428ea19cc00c97c5ca0e
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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