(4-(Morpholin-4-yl)phenyl)boronic acid → HCID 178451992, compound

HRID 2194578Notes

Reaction equation

HRID 2194578 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:14]=[C:13]([O:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:12](Br)=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[O:31]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=2)[CH2:33][CH2:32]1>>[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:14]=[C:13]([O:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:12]([C:40]3[CH:39]=[CH:38][C:37]([N:34]4[CH2:33][CH2:32][O:31][CH2:36][CH2:35]4)=[CH:42][CH:41]=3)=[CH:11][N:10]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 2795359(4-(Morpholin-4-yl)phenyl)boronic acidHCID 178451991HCID 178451991, compound

Product 1

HCID 178451992HCID 178451992, compoundYield 70%

Procedure

Using the procedure of Example 1 Step 3, tert-butyl 4-((2-(cis-4-methylcyclohexylamino)-5-bromopyrimidin-4-yloxy)methyl)piperidine-1-carboxylate was reacted with 4-morpholinophenylboronic acid to provide the title compound at 70% yield. 1H NMR (CDCl3, 400 MHz) 8.03 (s, 1H), 7.35 (d, 2H), 6.89 (d, 2H), 5.17 (sb, 1H), 4.16-4.03 (m, 6H), 3.83 (m, 4H), 3.15 (m, 4H), 2.66 (m, 2H), 1.91-1.44 (m, 11H), 1.41 (s, 9H), 0.95 (d, 3H); MS (ESI) m/z: Calc: 565.4 (M+). Found. 566.3 (M+1).

Sources & evidence

ORD record
ord-c9c9e15e2d47405195ca5b26d1b9c0e4
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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