(4-(Morpholin-4-yl)phenyl)boronic acid → HCID 178452153, compound

HRID 2194572Notes

Reaction equation

HRID 2194572 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[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]3)[C:12](Br)=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[O:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=2)[CH2:31][CH2:30]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[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]3)[C:12]([C:38]3[CH:37]=[CH:36][C:35]([N:32]4[CH2:31][CH2:30][O:29][CH2:34][CH2:33]4)=[CH:40][CH:39]=3)=[CH:11][N:10]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 2795359(4-(Morpholin-4-yl)phenyl)boronic acidHCID 178452152HCID 178452152, compound

Product 1

HCID 178452153HCID 178452153, compoundYield 78%

Procedure

Using the procedure of Example 1 Step 3, tert-butyl 3-((2-(cis-4-methylcyclohexylamino)-5-bromopyrimidin-4-yloxy)methyl)azetidine-1-carboxylate was reacted with 4-morpholinophenylboronic acid to provide the title compound at 78% yield. 1H NMR (CDCl3, 400 MHz) 8.02 (s, 1H), 7.30 (d, 2H), 6.85 (d, 2H), 5.38 (sb, 1H), 4.41 (d, 2H), 4.07-3.80 (m, 3H), 4.79-3.70 (m, 5H), 3.11-3.09 (m, 4H), 2.95-2.88 (m, 2H), 1.76-1.45 (m, 6H), 1.44 (s, 9H), 1.20-1.16 (m, 3H), 0.87 (d, 3H); MS (ESI) m/z: Calc: 537.3 (M+). Found. 538.3 (M+1).

Sources & evidence

ORD record
ord-498c4f9136874421b76f144bcf31eaf8
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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