5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → N-(5-(6-aminopyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

HRID 1924782Notes

Reaction equation

HRID 1924782 reaction equation
Br[C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11][C:12](=[O:24])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])=[CH:15][CH:14]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[CH:35][C:36]([NH2:39])=[N:37][CH:38]=2)O1>>[NH2:39][C:36]1[N:37]=[CH:38][C:33]([C:2]2[N:7]=[C:6]3[S:8][C:9]([NH:11][C:12](=[O:24])[C:13]4[CH:18]=[CH:17][C:16]([C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])=[CH:15][CH:14]=4)=[N:10][C:5]3=[CH:4][CH:3]=2)=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 58015383N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

Product 1

HCID 44548621N-(5-(6-aminopyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamideYield 22%

Procedure

The titled compound (yield=22%, white solid) was prepared using a procedure analogous to that described in connection with 10 (Example 10) except that 2F (Example 2) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27 (s, 6H) 3.17 (s, 2H) 3.49 (s, 1H) 7.03 (d, J=9.35 Hz, 1H) 7.58 (d, J=8.59 Hz, 2H) 7.89 (br. s., 2H) 8.08 (dd, J=11.12, 8.59 Hz, 3H) 8.24 (d, J=8.59 Hz, 1H) 8.62 (dd, J=9.35, 2.27 Hz, 1H) 8.72 (d, J=1.77 Hz, 1H) 13.02 (s, 1H); ESI-MS: m/z 420.0 (M+H)+.

Sources & evidence

ORD record
ord-fb47983a1c574faea653839017bd8477
Source dataset
uspto-grants-2012_05
Patent number
US08178555B2

Reaction notes

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