(4-cyano-cyclohexylmethyl)-amine → HCID 178511241, compound

HRID 1483851Notes

Reaction equation

HRID 1483851 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.[NH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][CH:23]([C:26]#[N:27])[CH2:22][CH2:21]1.[F-].[K+]>CS(C)=O>[Cl:17][C:13]1[CH:12]=[C:11]([C:8]2[N:6]3[N:7]=[C:2]([NH:27][CH2:26][C@H:23]4[CH2:24][CH2:25][C@H:20]([C:19]#[N:18])[CH2:21][CH2:22]4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 291897(4-cyano-cyclohexylmethyl)-amineHCID 522689Potassium FluorideHCID 574186866-Chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazine

Product 1

HCID 178511241HCID 178511241, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 6-chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazine (50 mg, 0.189 mmol), -4-(aminomethyl)cyclohexanecarbonitrile (111 mg, 0.25 mmol) and KF (47 mg, 0.82 mmol) in DMSO (0.5 mL) was heated at 130° C. overnight. LCMS showed the reaction was almost complete. The mixture was purified by prep. HPLC to give EX. 8-88 (26 mg, 38%) as an off-white solid.

Workup

  1. customThe mixture was purified by prep
  2. customHPLC to give EX

Sources & evidence

ORD record
ord-42394bca9a7b4d698f8b1e88baa9203d
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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