HCID 71558617, compound → HCID 71559220, compound

HRID 2203454Notes

Reaction equation

HRID 2203454 reaction equation
ClC1C=CC(O)=C(C2C=NN3C=CC=NC=23)C=1.[NH2:18][C:19]1[C:23]2[CH:24]=[C:25]([C:28]3[C:29]([O:34][C:35]4[C:40]([F:41])=[CH:39][C:38]([S:42]([N:45](CC5C=CC(OC)=CC=5OC)[C:46]5[S:50][N:49]=[CH:48][N:47]=5)(=[O:44])=[O:43])=[C:37]([F:62])[CH:36]=4)=[N:30][CH:31]=[CH:32][CH:33]=3)[CH:26]=[CH:27][C:22]=2[O:21][N:20]=1>>[NH2:18][C:19]1[C:23]2[CH:24]=[C:25]([C:28]3[C:29]([O:34][C:35]4[C:40]([F:41])=[CH:39][C:38]([S:42]([NH:45][C:46]5[S:50][N:49]=[CH:48][N:47]=5)(=[O:44])=[O:43])=[C:37]([F:62])[CH:36]=4)=[N:30][CH:31]=[CH:32][CH:33]=3)[CH:26]=[CH:27][C:22]=2[O:21][N:20]=1

Participants

3

Reactant 2

HCID 71558617HCID 71558617, compoundHCID 89544255HCID 89544255, compound

Product 1

HCID 71559220HCID 71559220, compoundYield 7%

Procedure

Following the procedure as described in EXAMPLE 44, making non-critical variations to replace 4-chloro-2-(pyrazolo[1,5-a]pyrimidin-3-yl)phenol with 4-((3-(3-aminobenzo[d]isoxazol-5-yl)pyridin-2-yl)oxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide, 4-((3-(3-aminobenzo[d]isoxazol-5-yl)pyridin-2-yl)oxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide was obtained as a colorless solid in 7% yield (0.01 g): 1H NMR (300 MHz, DMSO-d6) δ 8.52 (s, 1H), 8.18-8.10 (m, 2H), 8.02 (dd, J=7.5, 1.8 Hz, 1H), 7.87-7.77 (m, 2H), 7.69 (dd, J=10.0, 6.0 Hz, 1H), 7.57 (d, J=8.7 Hz, 1H), 7.36 (dd, J=7.4, 4.9 Hz, 1H), 6.51 (br s, 2H); MS (ES+) m/z 502.6 (M+1).

Sources & evidence

ORD record
ord-9233e75d404b4fba9970f77773a900ac
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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