2-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate → HCID 71008515, compound

HRID 1025561Notes

Reaction equation

HRID 1025561 reaction equation
Br[C:2]1[N:3]=[C:4]([C:8]([NH2:10])=[O:9])[N:5]([CH3:7])[CH:6]=1.[C:11]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[N:20]([C:26]1[CH:36]=[CH:35][CH:34]=[C:33](B3OC(C)(C)C(C)(C)O3)[C:27]=1[CH2:28][O:29]C(=O)C)[N:19]=[CH:18]2)([CH3:14])([CH3:13])[CH3:12]>>[C:11]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[N:20]([C:26]1[C:27]([CH2:28][OH:29])=[C:33]([C:2]3[N:3]=[C:4]([C:8]([NH2:10])=[O:9])[N:5]([CH3:7])[CH:6]=3)[CH:34]=[CH:35][CH:36]=1)[N:19]=[CH:18]2)([CH3:14])([CH3:12])[CH3:13]

Participants

3

Reactant 2

HCID 580162042-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate2×HCID 71008280HCID 71008280, compound

Product 1

HCID 71008515HCID 71008515, compoundYield 33%

Procedure

This compound was prepared with the same method as described in Example 1 by using 4-bromo-1-methyl-1H-imidazole-2-carboxylic acid amide (intermediate-1) and acetic acid 2-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl ester (intermediate 4). The desired compound was prepared in two steps (33% yield). 1H NMR (300 MHz, CDCl3) δ 8.46 (d, J=8.5 Hz, 1H), 8.36 (s, 1H), 7.95-7.91 (m, 2H), 7.77 (d, J=1.6 Hz, 1H), 7.70 (s, 1H), 7.54 (t, J=7.9 Hz, 1H), 7.36 (dd, J=7.9, 1.3 Hz, 1H), 4.42 (br s, 2H), 4.14 (s, 3H), 1.46 (s, 9H). LC-MS calcd for C24H25N5O3 (m/e) 431.20, obsd 432 [M+1]+.

Workup

  1. customThis compound was prepared with the same method

Sources & evidence

ORD record
ord-509bb6bed0c84c259af39368fae347e3
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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