1,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 73437704, compound

HRID 522009Notes

Reaction equation

HRID 522009 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][N:33]1[C:37]([CH3:38])=[C:36](B2OC(C)(C)C(C)(C)O2)[CH:35]=[N:34]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:36]3[CH:35]=[N:34][N:33]([CH3:32])[C:37]=3[CH3:38])[S:3][CH:4]=2)=[O:8])[CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 426473131,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 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 73437704HCID 73437704, compound

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 1,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole gave 242. 1H NMR (400 MHz, DMSO-d6) δ 9.61 (s, 1H), 8.24 (s, 1H), 7.95 (s, 1H), 7.83 (s, 1H), 4.84 (dd, J=10.6, 3.8 Hz, 1H), 4.55-4.32 (m, 1H), 4.28-4.14 (m, 1H), 4.13-3.94 (m, 1H), 3.81 (s, 3H), 3.78 (s, 3H), 3.29-3.16 (m, 1H), 2.61 (s, 3H), 2.12-2.02 (m, 1H), 1.91-1.78 (m, 1H), 1.75-1.64 (m, 4H). LCMS (ES+) m/z 434 (M+1).

Sources & evidence

ORD record
ord-700bdec4aa934d46b32e880adb2b3ee8
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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