Hydrochloric Acid → HCID 57654557, compound

HRID 1921629Notes

Reaction equation

HRID 1921629 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)=[N:9][N:10]=2)[N:7]=1.[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[N:22]1([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([CH2:11][C:12]4[CH:13]=[C:14]5[C:19](=[CH:20][CH:21]=4)[N:18]=[CH:17][CH:16]=[CH:15]5)=[N:9][N:10]=3)[N:7]=2)[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 11430Potassium CarbonateHCID 249683676-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

Product 1

HCID 57654557HCID 57654557, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline, imidazole, and potassium carbonate were stirred in DMF (3 mL) for 8 h at 100° C. Aqueous HCl (0.5 N) was added and the volatiles were removed in vacuo. Purification by HPLC (5-35% B over 45 min) yielded the product as a TFA salt. The residue was dissolved in aq 1N HCl (5 mL) and the volatiles removed in vacuo. After two repetitions, the product-dihydrochloride was dried under high vacuum to yield a glassy solid (53 mg, 44% yield). 1H-NMR (CD3OD): δ 9.60 (1H, s), 9.17 (1H, dd, J=1.5, 5.3 Hz), 9.10 (1H, m), 8.58 (1H, d, J=9.9 Hz), 8.38 (1H, m), 8.36 (1H, m), 8.27 (1H, m), 8.23 (1H, m), 8.05 (1H, dd, J=5.3, 8.3 Hz), 7.98 (1H, d, J=9.9 Hz), 7.72 (1H, s), 5.12 (2H, s), 4.98 (2H, m). ESI-MS (m/z): Calcd. for C18H13N7: 327.1; found: 328.3 (M+H).

Workup

  1. customthe volatiles were removed in vacuo
  2. customPurification by HPLC (5-35% B over 45 min)

Sources & evidence

ORD record
ord-6b597cc1978745f9972605e586a92bc1
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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