Ammonia → HCID 57932996, compound

HRID 1432663Notes

Reaction equation

HRID 1432663 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20](Br)=[N:19][C:18]=3[CH3:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[NH3:24]>CO.[Cu-]=O>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20]([NH2:24])=[N:19][C:18]=3[CH3:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 68840065HCID 68840065, compound

Product 1

HCID 57932996HCID 57932996, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

50 mg of 8-(1-ethyl-propyl)-3-[2-bromo-4-methyl-5-thiazolyl]-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.13 mmol) and 10 mg of copper (I) oxide are added to 3 ml of 2 M NH3 in MeOH and vial is capped with a Teflon® lined cap, heated at 130° C. for overnight. The reaction mixture is concentrated under N2 gas and applied onto a silica-gel chromatography column (Hexane:AcOEt:2 M NH3 in MeOH=20:20:1) to give 22 mg of the title compound. Yield 54%: mass spectrum (m/e): 330 (M+1); 1H-NMR (CDCl3): 6.72 (s, 1H), 5.24 (br, 2H), 3.40 (m, 1H), 2.56 (s, 3H), 2.47 (s, 3H), 2.18 (s, 3H), 1.85 (m, 4H), 0.90 (t, 6H, J=7.4 Hz).

Workup

  1. customlined cap
  2. concentrationThe reaction mixture is concentrated under N2 gas

Sources & evidence

ORD record
ord-fa024a879db5451099d7e0b97633d6b3
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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