4-Bromoisoxazole → HCID 90415738, compound

HRID 1776774Notes

Reaction equation

HRID 1776774 reaction equation
[CH3:1][C:2]([CH3:44])([CH2:6][C:7]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:15][CH:14]=2)[C:10]2[CH:28]=[CH:29][C:30]([O:32][CH2:33][C:34]3[CH:43]=[CH:42][C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[N:35]=3)=[CH:31][C:9]=2[N:8]=1)[C:3]([OH:5])=[O:4].Br[C:46]1[CH:47]=[N:48][O:49][CH:50]=1>>[O:49]1[CH:50]=[C:46]([C:16]2[CH:17]=[CH:18][C:13]([CH2:12][N:11]3[C:10]4[CH:28]=[CH:29][C:30]([O:32][CH2:33][C:34]5[CH:43]=[CH:42][C:41]6[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=6)[N:35]=5)=[CH:31][C:9]=4[N:8]=[C:7]3[CH2:6][C:2]([CH3:44])([CH3:1])[C:3]([OH:5])=[O:4])=[CH:14][CH:15]=2)[CH:47]=[N:48]1

Participants

3

Reactant 2

HCID 38622484-BromoisoxazoleHCID 90414533HCID 90414533, compound

Product 1

HCID 90415738HCID 90415738, compound

Procedure

The title compound was prepared with similar methods to those in Example 147 using 2,2-dimethyl-3-(5-(quinolin-2-ylmethoxy)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-1H-benzo[d]imidazol-2-yl)propanoic acid and 4-bromoisoxazole. MS (ESI): mass calcd. for C32H28N4O4, 532.21; m/z found, 533.2 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 9.18 (d, J=7.8, 1H), 9.08 (s, 1H), 8.82 (s, 1H), 8.42 (d, J=8.6, 1H), 8.35 (d, J=8.2, 1H), 8.24-8.17 (m, 2H), 7.98 (t, J=7.4, 1H), 7.67-7.64 (m, 4H), 7.45 (d, J=8.0, 1H), 7.34 (d, J=7.0, 2H), 5.88 (s, 4H), 3.59 (s, 2H), 1.44 (s, 6H).

Sources & evidence

ORD record
ord-0668605c462142d88463a66a3cd40aba
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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