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

HRID 1963956Notes

Reaction equation

HRID 1963956 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 lyophilized 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-9b86a91513724bfd98764ff0ed545c0c
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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