3-cyclopropyl-1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole → HCID 86713908, compound

HRID 522018Notes

Reaction equation

HRID 522018 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.[CH:32]1([C:35]2[C:39](B3OC(C)(C)C(C)(C)O3)=[CH:38][N:37]([CH3:49])[N:36]=2)[CH2:34][CH2:33]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:35]([CH:32]4[CH2:34][CH2:33]4)=[N:36][N:37]([CH3:49])[CH:38]=3)[S:3][CH:4]=2)=[O:8])[CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 601365313-cyclopropyl-1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazoleHCID 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 86713908HCID 86713908, 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 3-cyclopropyl-1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole gave 253. 1H NMR (400 MHz, DMSO-d6) δ 9.76 (s, 1H), 8.27 (s, 1H), 8.20 (s, 1H), 7.81 (s, 1H), 5.02-4.76 (m, 2H), 4.16-3.90 (m, 2H), 3.80 (s, 3H), 3.76 (s, 3H), 3.29-3.16 (m, 1H), 2.41-2.30 (m, 1H), 2.18-2.09 (m, 1H), 1.86-1.74 (m, 2H), 1.66-1.58 (m, 1H), 1.02-0.90 (m, 2H), 0.89-0.80 (m, 2H). LCMS (ES+) m/z 460 (M+1).

Sources & evidence

ORD record
ord-e5b3375f057c432fa439c496fb8ed467
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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