[1-Methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]boronic acid → HCID 86713907, compound

HRID 522017Notes

Reaction equation

HRID 522017 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[CH:37]=[C:36](B(O)O)[C:35]([C:41]([F:44])([F:43])[F:42])=[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[C:35]([C:41]([F:44])([F:43])[F:42])=[N:34][N:33]([CH3:32])[CH:37]=3)[S:3][CH:4]=2)=[O:8])[CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 53405559[1-Methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]boronic acidHCID 86713846tert-butyl ((3R,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate2×

Product 1

HCID 86713907HCID 86713907, compound

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-fluorooxepan-4-yl)carbamate (Intermediate 100), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)boronic acid gave 252. 1H NMR (400 MHz, DMSO-d6) δ 9.64 (s, 1H), 8.63 (s, 1H), 8.42 (s, 1H), 7.88 (s, 1H), 4.98-4.72 (m, 2H), 4.22-4.03 (m, 1H), 4.00 (s, 3H), 3.97-3.88 (m, 1H), 3.75 (s, 3H), 3.30-3.17 (m, 1H), 2.14-2.03 (m, 1H), 1.92-1.68 (m, 3H), 1.66-1.57 (m, 1H). LCMS (ES+) m/z 488 (M+1).

Sources & evidence

ORD record
ord-0474316b337245fd96754638afef197e
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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