tert-Butyl (3R)-3-(aminomethyl)piperidine-1-carboxylate → HCID 178451957, compound

HRID 1623412Notes

Reaction equation

HRID 1623412 reaction equation
[Cl:1][C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18](F)[N:17]=2)=[CH:4][C:5]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[NH2:23][CH2:24][C@H:25]1[CH2:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]1>CS(C)=O>[NH2:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([NH:8][C:5]2[CH:4]=[C:3]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH:23][CH2:24][C@H:25]4[CH2:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]4)[N:17]=3)[C:2]([Cl:1])=[CH:7][N:6]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 1502023tert-Butyl (3R)-3-(aminomethyl)piperidine-1-carboxylateHCID 178511586HCID 178511586, compound

Product 1

HCID 178451957HCID 178451957, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
102.5 °C

Procedure

A mixture of trans-N1-(5′-chloro-6-fluoro-2,4′-bipyridin-2′-yl)cyclohexane-1,4-diamine (Example 1a, step 2) (50 mg, 0.156 mmol), DMSO (0.75 ml), (R)-tert-butyl 3-(aminomethyl)piperidine-1-carboxylate (167 mg, 0.779 mmol) and TEA (0.033 ml, 0.234 mmol) was stirred at 100-105° C. for 40 hours and the reaction progress was followed by LCMS. The reaction mixture was let cool, added 0.75 ml of DMSO, filtered and purified by prep LC, and lyapholized to yield 36 mg of titled compound as a TFA salt. LCMS (m/z): 515.4 (MH+), retention time=0.64 min.;

Workup

  1. temperatureThe reaction mixture was let cool
  2. filtrationfiltered
  3. custompurified by prep LC

Sources & evidence

ORD record
ord-c956d9e74c944a08b1fc97a7a40d67b1
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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