2-(Trifluoromethyl)benzeneboronic acid → HCID 86713925, compound

HRID 522035Notes

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]([F:52])([F:51])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1B(O)O>>[NH2:32][C:4]1[S:3][C:2]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[C:41]([F:52])([F:51])[F:40])=[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 27343872-(Trifluoromethyl)benzeneboronic acid

HCID 86713830tert-butyl N-[2-bromo-4-[[5-[(2S,5R,6R)-5-(tert-butoxycarbonylamino)-6-fluoro-oxepan-2-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate2×

Product 1

HCID 86713925HCID 86713925, compound

Procedure

Following the procedure for Example 101 starting from tert-butyl N-[2-bromo-4-[[5-[(2S,5R,6R)-5-(tert-butoxycarbonylamino)-6-fluoro-oxepan-2-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate (Intermediate 88), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (2-(trifluoromethyl)phenyl)boronic acid gave 270. 1H NMR (400 MHz, DMSO-d6) δ 9.18 (s, 1H), 7.88 (t, J=8.7 Hz, 1H), 7.83 (s, 1H), 7.77 (dd, J=6.5, 1.5 Hz, 2H), 7.72-7.62 (m, 1H), 7.46 (s, 2H), 4.87 (dd, J=8.5, 3.4 Hz, 1H), 4.82-4.60 (m, 1H), 3.97-3.83 (m, 2H), 3.71 (s, 3H), 3.17 (ddt, J=23.0, 9.2, 2.5 Hz, 1H), 2.15-2.04 (m, 1H), 1.86-1.54 (m, 4H). LCMS (ES+) m/z 499 (M+1).

Sources & evidence

ORD record: ord-bc7a21ccadf64a948093f42bc9f456cf
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328106B2

Reaction notes

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