4-(4-chloro-2-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenoxy)-N-(2,4-dimethoxybenzyl)-3-fluoro-N-(pyrimidin-2-yl)benzenesulfonamide → 4-(4-chloro-2-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenoxy)-3-fluoro-N-(pyrimidin-2-yl)benzenesulfonamide

HRID 2203448Notes

Reaction equation

HRID 2203448 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:96]=[CH:95][C:65]([O:66][C:67]2[CH:72]=[CH:71][C:70]([S:73]([N:76](CC3C=CC(OC)=CC=3OC)[C:77]3[N:82]=[CH:81][CH:80]=[CH:79][N:78]=3)(=[O:75])=[O:74])=[CH:69][C:68]=2[F:94])=[C:64]([C:97]2[CH:98]=[CH:99][C:100]3[O:104][C:103](=[O:105])[NH:102][C:101]=3[CH:106]=2)[CH:63]=1>>[Cl:61][C:62]1[CH:96]=[CH:95][C:65]([O:66][C:67]2[CH:72]=[CH:71][C:70]([S:73]([NH:76][C:77]3[N:82]=[CH:81][CH:80]=[CH:79][N:78]=3)(=[O:74])=[O:75])=[CH:69][C:68]=2[F:94])=[C:64]([C:97]2[CH:98]=[CH:99][C:100]3[O:104][C:103](=[O:105])[NH:102][C:101]=3[CH:106]=2)[CH:63]=1

Participants

3

Reactant 2

HCID 903890654-(4-chloro-2-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenoxy)-N-(2,4-dimethoxybenzyl)-3-fluoro-N-(pyrimidin-2-yl)benzenesulfonamideHCID 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 715590714-(4-chloro-2-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenoxy)-3-fluoro-N-(pyrimidin-2-yl)benzenesulfonamideYield 50%

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 4-(4-chloro-2-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenoxy)-N-(2,4-dimethoxybenzyl)-3-fluoro-N-(pyrimidin-2-yl)benzenesulfonamide, 4-(4-chloro-2-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenoxy)-3-fluoro-N-(pyrimidin-2-yl)benzenesulfonamide was obtained a beige solid in 50% yield over two steps (0.054 g): 1H NMR (300 MHz, DMSO-d6) δ11.93 (br s, 1H), 11.69 (s, 1H), 8.50 (d, J=2.9 Hz, 2H), 7.83 (d, J=9.8 Hz, 1H), 7.66 (d, J=8.0 Hz, 1H), 7.59 (s, 1H), 7.49 (d, J=7.7 Hz, 1H), 7.29-7.01 (m, 6H); MS (ES+) m/z 512.8 (M+1), 514.8 (M+1).

Sources & evidence

ORD record
ord-3a3f22540d264f9fa00d423588f85f5c
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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