[3-Fluoro-2-(trifluoromethyl)phenyl]boronic acid → HCID 86713963, compound

HRID 522071Notes

Reaction equation

Br[C:2]1[S:3][C:4]([NH:32]C(=O)OC(C)(C)C)=[C:5]([C:7](=[O:31])[NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:30])[C:13]=2[C@@H:14]2[CH2:20][CH2:19][C@@H:18]([NH:21]C(OC(C)(C)C)=O)[C@H:17]([F:29])[CH2:16][O:15]2)[N:6]=1.[F:40][C:41]1[C:42]([C:50]([F:53])([F:52])[F:51])=[C:43](B(O)O)[CH:44]=[CH:45][CH:46]=1>>[NH2:32][C:4]1[S:3][C:2]([C:43]2[CH:44]=[CH:45][CH:46]=[C:41]([F:40])[C:42]=2[C:50]([F:51])([F:53])[F:52])=[N:6][C:5]=1[C:7]([NH:8][C:9]1[CH:10]=[N:11][N:12]([CH3:30])[C:13]=1[C@@H:14]1[CH2:20][CH2:19][C@@H:18]([NH2:21])[C@H:17]([F:29])[CH2:16][O:15]1)=[O:31]

Participants

Reactant 2

HCID 17749939[3-Fluoro-2-(trifluoromethyl)phenyl]boronic acid

HCID 86713840tert-butyl N-[2-bromo-4-[[5-[(2S,5R,6S)-5-(tert-butoxycarbonylamino)-6-fluoro-oxepan-2-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate2×

Product 1

HCID 86713963HCID 86713963, compound

Procedure

Following the procedure for Example 101 starting from tert-butyl N-[2-bromo-4-[[5-[(2S,5R,6S)-5-(tert-butoxycarbonylamino)-6-fluoro-oxepan-2-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate (Intermediate 95), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (3-fluoro-2-(trifluoromethyl)phenyl)boronic acid gave 336. 1H NMR (400 MHz, DMSO-d6) δ 9.13 (s, 1H), 7.85-7.77 (m, 1H), 7.72 (s, 1H), 7.66-7.57 (m, 1H), 7.54 (d, J=7.8 Hz, 1H), 7.44 (s, 2H), 4.81-4.73 (m, 1H), 4.63-4.44 (m, 1H), 4.22-4.10 (m, 1H), 4.08-3.91 (m, 1H), 3.76 (s, 3H), 2.10-2.00 (m, 1H), 1.90-1.73 (m, 3H). LCMS (ES+) m/z 517 (M+1).

Sources & evidence

ORD record: ord-c82c2474aa1b4081b08c85eedcf3ecce
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328106B2

Reaction notes

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