(R)-tert-butyl 3-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)pyrrolidine-1-carboxylate → HCID 178452027, compound

HRID 2194565Notes

Reaction equation

HRID 2194565 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH2:10][C@@H:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:23][C@@H:24]1[CH2:29][CH2:28][C@H:27]([NH2:30])[CH2:26][CH2:25]1>>[CH3:23][C@@H:24]1[CH2:29][CH2:28][C@H:27]([NH:30][C:5]2[N:4]=[C:3]([O:9][CH2:10][C@@H:11]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)[C:2]([Br:1])=[CH:7][N:6]=2)[CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 86761725(R)-tert-butyl 3-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)pyrrolidine-1-carboxylateHCID 178461304HCID 178461304, compound

Product 1

HCID 178452027HCID 178452027, compoundYield 55%

Procedure

Using the procedure of Example 1 Step 2, (R)-tert-butyl 3-((5-bromo-2-chloropyrimidin-4-yloxy)methyl)pyrrolidine-1-carboxylate was reacted with cis-4-methylcyclohexanamine to provide the title compound at 55% yield. 1H NMR (CDCl3, 400 MHz) δ 8.06 (s, 1H), 5.13 (sb, 1H), 4.28 (m, 2H), 3.96 (m, 1H), 3.60-3.15 (m, 4H), 2.66 (m, 1H), 2.02 (m, 1H), 1.77-1.58 (m, 7H), 1.44 (s, 9H), 1.28-1.16 (m, 3H), 0.91 (d, 3H); MS (ESI) m/z: Calc: 544.2 (M+). Found. 545.2 (M+1).

Sources & evidence

ORD record
ord-081703669ba34f14aa85ea35f21f0c54
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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