HCID 178458066, compound → HCID 178457504, compound

HRID 1483829Notes

Reaction equation

HRID 1483829 reaction equation
[N:1]([C:4]([C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=4)=[CH:21][N:22]=3)[N:19]=2)[CH2:9][CH2:8]1)([CH3:6])[CH3:5])=[N+]=[N-]>CO.C(Cl)Cl.[Pd]>[NH2:1][C:4]([C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=4)=[CH:21][N:22]=3)[N:19]=2)[CH2:9][CH2:8]1)([CH3:6])[CH3:5]

Participants

5

Reactant 1

HCID 178458066HCID 178458066, compound

Product 1

HCID 178457504HCID 178457504, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(trans-4-(2-azidopropan-2-yl)cyclohexyl)-3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-amine (90 mg, 0.22 mmol) and Pd/C (30 mg) in MeOH (5 mL) and CH2Cl2 (5 mL) was hydrogenated under 50 psi of H2 at room temperature for 48 h. LCMS showed the reaction was complete. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by prep. HPLC to give EX. 8-79 (4 mg, 5%) as an off-white solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by prep
  4. customHPLC to give EX

Sources & evidence

ORD record
ord-52d1b7ec39d440eb955fa0ba05bb0f57
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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