(2-Methoxypyridin-3-yl)boronic acid → N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2-methoxypyridin-3-yl)thiazole-4-carboxamide

HRID 522000Notes

Reaction equation

HRID 522000 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]([CH3:31])[C:14]=2[C@H:15]2[O:21][CH2:20][C@@H:19]([F:22])[C@H:18]([NH:23]C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[O:8])[N:6]=1.[CH3:32][O:33][C:34]1[C:39](B(O)O)=[CH:38][CH:37]=[CH:36][N:35]=1>>[NH2:23][C@H:18]1[C@H:19]([F:22])[CH2:20][O:21][C@H:15]([C:14]2[N:13]([CH3:31])[N:12]=[CH:11][C:10]=2[NH:9][C:7]([C:5]2[N:6]=[C:2]([C:39]3[C:34]([O:33][CH3:32])=[N:35][CH:36]=[CH:37][CH:38]=3)[S:3][CH:4]=2)=[O:8])[CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 86713845tert-butyl ((3S,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate2×

Product 1

HCID 73438525N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2-methoxypyridin-3-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-fluorooxepan-4-yl)carbamate (Intermediate 99), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (2-methoxypyridin-3-yl)boronic acid gave 232. LCMS (ES+) m/z 447 (M+1).

Sources & evidence

ORD record
ord-ce132cf6cc554c5aadef6ecf8f6f407c
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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