Tert-butyl 4-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)piperidine-1-carboxylate → HCID 178451991, compound

HRID 2194577Notes

Reaction equation

HRID 2194577 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:24][C@@H:25]1[CH2:30][CH2:29][C@H:28]([NH2:31])[CH2:27][CH2:26]1>>[CH3:24][C@@H:25]1[CH2:30][CH2:29][C@H:28]([NH:31][C:5]2[N:4]=[C:3]([O:9][CH2:10][CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[C:2]([Br:1])=[CH:7][N:6]=2)[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 86761727Tert-butyl 4-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)piperidine-1-carboxylateHCID 178461304HCID 178461304, compound

Product 1

HCID 178451991HCID 178451991, compoundYield 50%

Procedure

Using the procedure of Example 1 Step 2 tert-butyl 4-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)piperidine-1-carboxylate was reacted with cis-4-methylcyclohexanamine to provide the title compound in 50% yield. 1H NMR (CDCl3, 400 MHz) 8.05 (s, 1H), 5.10 (sb, 1H), 4.15 (m, 4H), 3.96 (m, 1H), 2.71 (m, 2H), 1.95 (m, 1H), 1.78-1.48 (m, 9H), 1.44 (s, 9H), 1.28-1.16 (m, 3H), 0.91 (d, 3H); MS (ESI) m/z: Calc: 482.2 (M+). Found. 484.2 (M++2).

Sources & evidence

ORD record
ord-2175d5a43f6e41999a06988428e73f30
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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