2-Bromo-1,3-thiazole-4-carboxamide → 2-[3-(6-tert-Butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-thiazole-4-carboxylic acid amide

HRID 1025562Notes

Reaction equation

HRID 1025562 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([NH2:9])=[O:8])[N:6]=1.[C:10]([C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[N:19]([C:25]1[CH:35]=[CH:34][CH:33]=[C:32](B3OC(C)(C)C(C)(C)O3)[C:26]=1[CH2:27][O:28]C(=O)C)[N:18]=[CH:17]2)([CH3:13])([CH3:12])[CH3:11]>>[C:10]([C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[N:19]([C:25]1[C:26]([CH2:27][OH:28])=[C:32]([C:2]3[S:3][CH:4]=[C:5]([C:7]([NH2:9])=[O:8])[N:6]=3)[CH:33]=[CH:34][CH:35]=1)[N:18]=[CH:17]2)([CH3:13])([CH3:11])[CH3:12]

Participants

3

Reactant 2

HCID 457896322-Bromo-1,3-thiazole-4-carboxamideHCID 580162042-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate2×

Product 1

HCID 710080202-[3-(6-tert-Butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-thiazole-4-carboxylic acid amideYield 25%

Procedure

This compound was prepared with the same method as described in Example 1 by using 2-bromothiazole-4-carboxylic acid amide (intermediate-2) 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 (25% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.56 (s, 1H), 8.41 (s, 1H), 8.24 (d, J=8.4 Hz, 1H), 8.05-8.00 (m, 2H), 7.82 (dd, J=1.8, 7.2 Hz, 1H), 7.61-7.58 (m, 2H), 4.54-4.45 (m, 2H), 1.41 (s, 9H). LC-MS calcd for C23H22N4O3S (m/e) 434.14, obsd 435 [M+1]+.

Workup

  1. customThis compound was prepared with the same method

Sources & evidence

ORD record
ord-5eff74844b1e4abf9bdaf9a4e6f69fb6
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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