HCID 89544255, compound → HCID 71558618, compound

HRID 2203434Notes

Reaction equation

HRID 2203434 reaction equation
ClC1C=CC(O)=C(C2C=NN3C=CC=NC=23)C=1.C(C1C2C([N:31]([C:35]3[C:39]4[C:40](C(C)(C)C)=[C:41]([C:44]5[CH:49]=[C:48]([Cl:50])[CH:47]=[CH:46][C:45]=5[O:51][C:52]5[CH:57]=[C:56]([F:58])[C:55]([S:59]([N:62]6[CH:66]=[CH:65][CH:64]=[N:63]6)(=[O:61])=[O:60])=[CH:54][C:53]=5[F:67])[CH:42]=[CH:43][C:38]=4[O:37][N:36]=3)C(=O)[O-])=NOC=2C=CC=1C1C=C(Cl)C=CC=1OC1C=C(F)C(S(N2C=CC=N2)(=O)=O)=CC=1F)(C)(C)C>>[N:62]1([S:59]([C:55]2[C:56]([F:58])=[CH:57][C:52]([O:51][C:45]3[CH:46]=[CH:47][C:48]([Cl:50])=[CH:49][C:44]=3[C:41]3[CH:42]=[CH:43][C:38]4[O:37][N:36]=[C:35]([NH2:31])[C:39]=4[CH:40]=3)=[C:53]([F:67])[CH:54]=2)(=[O:60])=[O:61])[CH:66]=[CH:65][CH:64]=[N:63]1

Participants

3

Reactant 2

HCID 89544255HCID 89544255, compoundHCID 131735788HCID 131735788, compound

Product 1

HCID 71558618HCID 71558618, compoundYield 2%

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 bis(tert-butyl (5-(2-(4-((1H-pyrazol-1-yl)sulfonyl)-2,5-difluorophenoxy)-5-chlorophenyl)benzo[d]isoxazol-3-yl))carbamate (0.36 g, 0.52 mmol), 5-(2-(4-((1H-pyrazol-1-yl)sulfonyl)-2,5-difluorophenoxy)-5-chlorophenyl)benzo[d]isoxazol-3-amine was obtained as a colorless solid in 2% yield (0.005 g): 1H NMR (300 MHz, CDCl3) δ 8.11-8.10 (m, 1H), 7.78 (dd, J=6.4, 9.3 Hz, 1H), 7.72 (s, 1H), 7.62-7.59 (m, 2H), 7.50 (d, J=2.4 Hz, 1H), 7.41-7.37 (m, 2H), 7.08 (d, J=8.6 Hz, 1H), 6.40-6.35 (m, 2H) (NH not observed); MS (ES+) m/z 502.7 (M+1), 504.7 (M+1).

Sources & evidence

ORD record
ord-c59e240c74684ee18ccd8628e9162378
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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