Di-tert-butyl (5-{5-chloro-2-[2-chloro-5-fluoro-4-(1,3-thiazol-4-ylsulfamoyl)phenoxy]phenyl}-1,2-benzoxazol-3-yl)imidodicarbonate → 4-(2-(3-aminobenzo[d]isoxazol-5-yl)-4-chlorophenoxy)-5-chloro-2-fluoro-N-(thiazol-4-yl)benzenesulfonamide

HRID 2203436Notes

Reaction equation

HRID 2203436 reaction equation
ClC1C=CC(OC2C=C(F)C(S(=O)(=O)N(CC3C=CC(OC)=CC=3OC)C3SN=CN=3)=CC=2F)=C(C2C=CC3ON=C(N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)C=3C=2)C=1.[Cl:61][C:62]1[CH:63]=[CH:64][C:65]([O:92][C:93]2[CH:98]=[C:97]([F:99])[C:96]([S:100](=[O:108])(=[O:107])[NH:101][C:102]3[N:103]=[CH:104][S:105][CH:106]=3)=[CH:95][C:94]=2[Cl:109])=[C:66]([C:68]2[CH:69]=[CH:70][C:71]3[O:75][N:74]=[C:73]([N:76](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C:72]=3[CH:91]=2)[CH:67]=1>C(OCC)C>[NH2:76][C:73]1[C:72]2[CH:91]=[C:68]([C:66]3[CH:67]=[C:62]([Cl:61])[CH:63]=[CH:64][C:65]=3[O:92][C:93]3[C:94]([Cl:109])=[CH:95][C:96]([S:100]([NH:101][C:102]4[N:103]=[CH:104][S:105][CH:106]=4)(=[O:107])=[O:108])=[C:97]([F:99])[CH:98]=3)[CH:69]=[CH:70][C:71]=2[O:75][N:74]=1

Participants

4

Reactant 2

HCID 123275483Di-tert-butyl (5-{5-chloro-2-[2-chloro-5-fluoro-4-(1,3-thiazol-4-ylsulfamoyl)phenoxy]phenyl}-1,2-benzoxazol-3-yl)imidodicarbonateHCID 123740120Di-tert-butyl [5-(5-chloro-2-{4-[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)sulfamoyl]-2,5-difluorophenoxy}phenyl)-1,2-benzoxazol-3-yl]imidodicarbonate

Product 1

HCID 715587694-(2-(3-aminobenzo[d]isoxazol-5-yl)-4-chlorophenoxy)-5-chloro-2-fluoro-N-(thiazol-4-yl)benzenesulfonamideYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following the procedure as described in EXAMPLE 44, making non-critical variations to replace di-tert-butyl [5-(5-chloro-2-{4-[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)sulfamoyl]-2,5-difluorophenoxy}phenyl)-1,2-benzoxazol-3-yl]imidodicarbonate with di-tert-butyl (5-{5-chloro-2-[2-chloro-5-fluoro-4-(1,3-thiazol-4-ylsulfamoyl)phenoxy]phenyl}-1,2-benzoxazol-3-yl)imidodicarbonate, 4-(2-(3-aminobenzo[d]isoxazol-5-yl)-4-chlorophenoxy)-5-chloro-2-fluoro-N-(thiazol-4-yl)benzenesulfonamide was obtained as an off-white solid in 83% yield (0.230 g) after trituration in diethyl ether (10 mL): 1H NMR (300 MHz, DMSO-d6) δ11.36 (s, 1H), 8.86-8.84 (m, 1H), 7.97 (s, 1H), 7.81 (d, J=7.1 Hz, 1H), 7.65-7.59 (m, 2H), 7.54 (dd, J=8.6, 2.0 Hz, 1H), 7.42 (d, J=8.7 Hz, 1H), 7.31 (d, J=8.7 Hz, 1H), 7.03-7.00 (m, 1H), 6.95 (d, J=10.8 Hz, 1H), 6.45 (br s, 2H); MS (ES+) m/z 550.7 (M+1), 552.7 (M+1).

Sources & evidence

ORD record
ord-2dc98ea8271745ea93e6fbe3a6985143
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

Loading…