Hydrochloric Acid → HCID 57932968, compound

HRID 1432680Notes

Reaction equation

HRID 1432680 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20]([N:22]4[CH2:31][CH2:30][C:25]5(OCC[O:26]5)[CH2:24][CH2:23]4)=[N:19][C:18]=3[CH3:32])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].Cl.C([O-])(O)=O.[Na+]>>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20]([N:22]4[CH2:31][CH2:30][C:25](=[O:26])[CH2:24][CH2:23]4)=[N:19][C:18]=3[CH3:32])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68841488HCID 68841488, compound

Product 1

HCID 57932968HCID 57932968, compoundYield 53.8%

Procedure

70 mg of 8-{5-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-4-methyl-thiazol-2-yl}-1,4-dioxa-8-aza-spiro[4.5]decane (0.15 mmol) is dissolved in 10. ml of conc. HCl and stirred at room temperature for 2 h. The reaction mixture is neutralized with sat. NaHCO3, extracted with CH2Cl2, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt=2:1) to give 33.2 mg of the title compound. Yield 52%. mass spectrum (m/e): 412 (M+1) 1H NMR (CDCl3): δ 6.70 (s, 1H), 3.94 (t, J=6.2 Hz, 4H), 3.35 (m, 1H), 2.67 (t, J=6.5 Hz, 4H), 2.57 (s, 3H), 2.47 (s, 3H), 2.21 (s, 3H), 1.86 (m, 4H), 0.91 (t, J=7.1 Hz, 6H).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-e869134074b2474fa058cb9f860d6ff8
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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