2-Aminothiazole → 5-(2-chloro-4-(trifluoromethyl)phenyl)-N-(oxazol-2-yl)naphthalene-2-sulfonamide

HRID 1473314Notes

Reaction equation

HRID 1473314 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16]([S:22](OC1C(F)=C(F)C(F)=C(F)C=1F)(=[O:24])=[O:23])=[CH:17]2.[O:37]1[CH:41]=[CH:40][N:39]=[C:38]1[NH2:42].S1C=CN=C1N>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16]([S:22]([NH:42][C:38]1[O:37][CH:41]=[CH:40][N:39]=1)(=[O:23])=[O:24])=[CH:17]2

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 5585212-AminooxazoleHCID 86687371Perfluorophenyl 5-(2-chloro-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate

Product 1

HCID 715861295-(2-chloro-4-(trifluoromethyl)phenyl)-N-(oxazol-2-yl)naphthalene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This product was prepared as described in EXAMPLE 41, using perfluorophenyl 5-(2-chloro-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate and oxazole-2-amine instead of perfluorophenyl 5-bromonaphthalene-2-sulfonate and thiazole-2-amine. The residue was taken up in minimal CH2Cl2 and absorbed onto a 5 g loading cartridge and passed through a silica gel column (12 g) using a gradient from 5% to 100% EtOAc to Heptanes and then triturated with an IPA/DCM/Heptanes mixture to give desired product 5-(2-chloro-4-(trifluoromethyl)phenyl)-N-(oxazol-2-yl)naphthalene-2-sulfonamide (0.010 g, 0.022 mmol) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 6.88 (d, J=1.76 Hz, 2H) 7.09 (d, J=1.76 Hz, 1H) 7.45-7.60 (m, 3H) 7.62-7.78 (m, 2H) 7.82-7.96 (m, 2H) 8.08 (d, J=8.61 Hz, 1H) 8.60 (d, J=1.76 Hz, 1H); m/z (ESI, +ve ion) 453.0 (M+H)+.

Workup

  1. customThis product was prepared
  2. customabsorbed onto a 5 g loading cartridge
  3. customtriturated with an IPA/DCM/Heptanes mixture

Sources & evidence

ORD record
ord-0e3bb0e316dd4f3e8741ebc316eccbf0
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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