2,3,6-Trifluorophenylboronic acid → N-(5-((2S,5R,6R)-5-amino-6-methoxyoxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2,3,6-trifluorophenyl)thiazole-4-carboxamide

HRID 522023Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C:10]2[CH:11]=[N:12][N:13]([CH3:32])[C:14]=2[C@H:15]2[O:21][CH2:20][C@H:19]([O:22][CH3:23])[C@H:18]([NH:24]C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[O:8])[N:6]=1.[F:33][C:34]1[C:39]([F:40])=[CH:38][CH:37]=[C:36]([F:41])[C:35]=1B(O)O>>[NH2:24][C@H:18]1[C@@H:19]([O:22][CH3:23])[CH2:20][O:21][C@H:15]([C:14]2[N:13]([CH3:32])[N:12]=[CH:11][C:10]=2[NH:9][C:7]([C:5]2[N:6]=[C:2]([C:35]3[C:36]([F:41])=[CH:37][CH:38]=[C:39]([F:40])[C:34]=3[F:33])[S:3][CH:4]=2)=[O:8])[CH2:16][CH2:17]1

Participants

Reactant 2

HCID 41606152,3,6-Trifluorophenylboronic acid

HCID 86713847tert-butyl ((3R,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-methoxyoxepan-4-yl)carbamate2×

Product 1

HCID 86713913N-(5-((2S,5R,6R)-5-amino-6-methoxyoxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2,3,6-trifluorophenyl)thiazole-4-carboxamide

Procedure

Following the procedure for Example 101 starting from tert-butyl ((3R,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-methoxyoxepan-4-yl)carbamate (Intermediate 101), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (2,3,6-trifluorophenyl)boronic acid gave 258. 1H NMR (400 MHz, DMSO-d6) δ 10.15 (s, 1H), 8.69 (s, 1H), 7.95 (s, 1H), 7.77 (qd, J=9.4, 4.9 Hz, 1H), 7.49-7.38 (m, 1H), 5.12 (t, J=5.6 Hz, 1H), 3.91-3.76 (m, 2H), 3.71 (s, 3H), 3.46-3.36 (m, 1H), 3.32-3.21 (m, 1H), 3.01 (s, 3H), 2.49-2.36 (m, 1H), 1.73-1.49 (m, 3H), 1.41 (br, 2H). LCMS (ES+) m/z 482 (M+1).

Sources & evidence

ORD record: ord-2ec8233d62154d98a3eda5a0af125d10
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328106B2

Reaction notes

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