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

HRID 522076Notes

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.[CH3:33][C:34]1[C:35](B(O)O)=[N:36][CH:37]=[CH:38][CH:39]=1>>[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:34]([CH3:33])=[CH:39][CH:38]=[CH:37][N:36]=3)[S:3][CH:4]=2)=[O:8])[CH2:16][CH2:17]1

Participants

Reactant 2

HCID 177502713-Methyl-2-pyridineboronic acid

HCID 86713848tert-butyl ((3S,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-methoxyoxepan-4-yl)carbamate2×

Product 1

HCID 86713968N-(5-((2S,5R,6S)-5-amino-6-methoxyoxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(3-methylpyridin-2-yl)thiazole-4-carboxamide

Procedure

Following the procedure for Example 101 starting from tert-butyl ((3S,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-methoxyoxepan-4-yl)carbamate (Intermediate 102), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (3-methylpyridin-2-yl)boronic acid gave 348. 1H NMR (500 MHz, DMSO-d6) δ 9.67 (s, 1H), 8.52-8.51 (m, 1H), 8.27 (s, 1H), 8.23 (s, 1H), 7.67-7.65 (m, 1H), 7.29-7.26 (m, 1H), 5.03-5.00 (m, 1H), 4.04-3.93 (m, 2H), 3.78 (s, 3H), 3.56-3.54 (m, 1H), 3.38-3.36 (m, 1H), 3.33 (s, 3H), 2.88 (s, 3H), 2.61 (s, 2H), 2.13-2.09 (m, 1H), 1.98-1.70 (m, 2H), 1.68-1.56 (m, 1H). LCMS (ES+) m/z 443 (M+1).

Sources & evidence

ORD record: ord-94b32cf5c59341538d959fb6ddb358e9
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328106B2

Reaction notes

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