4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole → 2-(1-{[2-(2h-Indazol-4-Yl)-4-(Morpholin-4-Yl)pyrido[3,2-D]pyrimidin-6-Yl]methyl}piperidin-4-Yl)propan-2-Ol

HRID 2091843Notes

Reaction equation

HRID 2091843 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]2[N:11]=[C:10]([CH2:12][N:13]3[CH2:18][CH2:17][CH:16]([C:19]([OH:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:37]2[CH:45]=[CH:44][CH:43]=[C:42]3[C:38]=2[CH:39]=[N:40][NH:41]3)O1>>[NH:41]1[C:42]2[C:38](=[C:37]([C:2]3[N:3]=[C:4]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[C:5]4[N:11]=[C:10]([CH2:12][N:13]5[CH2:18][CH2:17][CH:16]([C:19]([OH:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]5)[CH:9]=[CH:8][C:6]=4[N:7]=3)[CH:45]=[CH:44][CH:43]=2)[CH:39]=[N:40]1

Participants

3

Reactant 2

HCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 584049702-(1-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol

Product 1

HCID 533781562-(1-{[2-(2h-Indazol-4-Yl)-4-(Morpholin-4-Yl)pyrido[3,2-D]pyrimidin-6-Yl]methyl}piperidin-4-Yl)propan-2-Ol

Procedure

2-(1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol from Example 8 (88 mg) was reacted with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole via General Procedure A to produce 29.6 mg of 110 following reverse phase hplc purification. MS (Q1) 488.3 (M)+

Workup

  1. customto produce
  2. custom29.6 mg of 110 following reverse phase hplc purification

Sources & evidence

ORD record
ord-fdf1c3ca47ac47df888987eea8bda755
Source dataset
uspto-grants-2013_05
Patent number
US08440651B2

Reaction notes

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