(4-(Morpholin-4-yl)phenyl)boronic acid → HCID 178452028, compound

HRID 2194566Notes

Reaction equation

HRID 2194566 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][C@@H:17]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]3)[C:12](Br)=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[O:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=2)[CH2:32][CH2:31]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][C@@H:17]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]3)[C:12]([C:39]3[CH:38]=[CH:37][C:36]([N:33]4[CH2:32][CH2:31][O:30][CH2:35][CH2:34]4)=[CH:41][CH:40]=3)=[CH:11][N:10]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 2795359(4-(Morpholin-4-yl)phenyl)boronic acidHCID 178452027HCID 178452027, compound

Product 1

HCID 178452028HCID 178452028, compoundYield 85%

Procedure

Using the procedure of Example 1 Step 3, (R)-tert-butyl 3-((2-(cis-4-methylcyclohexylamino)-5-bromopyrimidin-4-yloxy)methyl)pyrrolidine-1-carboxylate with 4-morpholinophenylboronic acid to provide the title compound at 85% yield. 1H NMR (CDCl3, 400 MHz) δ 8.05 (s, 1H), 7.36 (d, 2H), 6.92 (d, 2H), 5.16 (sb, 1H), 4.30-4.27 (m, 2H), 4.10-4.01 (m, 1H), 386-3.84 (m, 4H), 3.60-3.12 (m, 8H); 2.70-2.62 (m, 1H), 2.05-1.98 (m, 1H), 1.81-1.46 (m, 8H), 1.44 (s, 9H), 1.29-1.21 (m, 3H), 0.93 (d, 3H); MS (ESI) m/z: Found: 552.3 (M+1); Calc: 551.4 (M+).

Sources & evidence

ORD record
ord-67f4edb0a9ba448a81191097242fda3f
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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