2-Bromo-1,3-thiazole-4-carboxamide → HCID 71008577, compound

HRID 1025564Notes

Reaction equation

HRID 1025564 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](=[C:22]([F:24])[CH:23]=1)[C:20](=[O:25])[N:19]([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:18]=[CH:17]2)([CH3:13])([CH3:12])[CH3:11]>>[C:10]([C:14]1[CH:15]=[C:16]2[C:21](=[C:22]([F:24])[CH:23]=1)[C:20](=[O:25])[N:19]([C:26]1[C:27]([CH2:28][OH:29])=[C:33]([C:2]3[S:3][CH:4]=[C:5]([C:7]([NH2:9])=[O:8])[N:6]=3)[CH:34]=[CH:35][CH:36]=1)[N:18]=[CH:17]2)([CH3:13])([CH3:11])[CH3:12]

Participants

3

Reactant 2

HCID 457896322-Bromo-1,3-thiazole-4-carboxamideHCID 594737692-(6-(tert-Butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate2×

Product 1

HCID 71008577HCID 71008577, compoundYield 10%

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-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl ester (intermediate 5). The desired compound was prepared in two steps (10% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.59 (d, J=2.4 Hz, 1H), 8.46 (s, 1H), 7.94 (d, J=1.8 Hz, 1H), 7.88-7.79 (m, 2H), 7.66-7.63 (m, 2H), 4.61-4.52 (m, 2H), 1.46 (s, 9H). LC-MS calcd for C23H21FN4O3S 452.13, obsd 453 [M+1]+.

Workup

  1. customThis compound was prepared with the same method

Sources & evidence

ORD record
ord-ba11c025a60a47b186930688578a8e50
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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