3-Amino-5-methylisoxazole → 5-(4-chloro-2-methoxyphenyl)-N-(5-methylisoxazol-3-yl)naphthalene-2-sulfonamide

HRID 1473304Notes

Reaction equation

HRID 1473304 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([NH2:7])[CH:3]=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[CH:17]=[CH:18][C:19]([S:25](Cl)(=[O:27])=[O:26])=[CH:20]3)=[C:11]([O:29][CH3:30])[CH:10]=1>>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[CH:17]=[CH:18][C:19]([S:25]([NH:7][C:4]2[CH:3]=[C:2]([CH3:1])[O:6][N:5]=2)(=[O:26])=[O:27])=[CH:20]3)=[C:11]([O:29][CH3:30])[CH:10]=1

Participants

3

Reactant 2

HCID 661723-Amino-5-methylisoxazoleHCID 866873615-(4-Chloro-2-methoxyphenyl)naphthalene-2-sulfonyl chloride

Product 1

HCID 866873625-(4-chloro-2-methoxyphenyl)-N-(5-methylisoxazol-3-yl)naphthalene-2-sulfonamideYield 31,862.699%

Procedure

This product was prepared as described in Example 43, employing 5-methylisoxazol-3-amine (48.0 mg, 0.49 mmol) and 5-(4-chloro-2-methoxyphenyl)naphthalene-2-sulfonyl chloride (0.498 μl, 0.408 μmol) to provide 5-(4-chloro-2-methoxyphenyl)-N-(5-methylisoxazol-3-yl)naphthalene-2-sulfonamide (55.8 mg, 0.13 mmol) as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.27 (s, 3H), 3.67 (s, 3H), 6.19 (s, 1H), 7.12-7.21 (m, 1H), 7.23-7.31 (m, 2H), 7.53-7.64 (m, 2H), 7.69-7.81 (m, 2H), 8.21 (d, J=8.30 Hz, 1H), 8.59 (d, J=1.78 Hz, 1H), 11.55 (br. s., 1H); m/z (ESI, +ve ion) 429.9 (M+H)+.

Workup

  1. customThis product was prepared

Sources & evidence

ORD record
ord-c6e36c7de1774d939b5be7fdf472706f
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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