Dimethylformamide → HCID 57752712, compound

HRID 226033Notes

Reaction equation

HRID 226033 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13](C3C4C(=C(C)C=CC=4)NC=3)=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[CH3:27][N:28]([CH:30]=O)[CH3:29].[H-].[Na+].CI>CCOC(C)=O>[CH3:27][N:28]1[C:29]2[C:1](=[CH:3][CH:6]=[CH:11][C:10]=2[CH3:12])[CH:2]=[C:30]1[C:13]1[N:8]2[N:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:7]2=[N:15][C:14]=1[CH3:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136360173HCID 136360173, compound

Product 1

HCID 57752712HCID 57752712, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-(1-ethyl-propyl)-2,6-dimethyl-3-(7-methyl-1H-indol-3-yl)-imidazo[1,2-b]pyridazine (0.037 g, 0.11 mmol) and DMF (2 mL) is added 60% NaH (0.005 g, 0.13 mmol). The solution is stirred for 30 minutes and MeI (0.008 mL, 0.13 mmol) is added. The solution is stirred for 1 h, diluted with EtOAc (20 mL), washed with water (2×10 mL), brine (10 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO (30%-50% EtOAc gradient) to furnish the title compound (0.025 g, 0.069 mmol, 66%). 1H NMR (CDCl3), δ 0.91 (t, J=7.5 Hz, 6H), 1.77-1.95 (m, 4H), 2.48 (s, 3H), 2.53 (s, 3H), 2.83 (s, 3H), 3.35-3.44 (m, 1H), 4.17 (s, 3H), 6.62 (s, 1H), 6.94-7.01 (m, 2H), 7.25 (s, 1H), 7.30 (dd, J=7.6, 1.3 Hz, 1H). LC/MS (m/z): calcd. for C23H28N4 (M+H)+: 361.6. found: 361.2.

Workup

  1. stirringThe solution is stirred for 1 h
  2. washwashed with water (2×10 mL), brine (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by ISCO (30%-50% EtOAc gradient)

Sources & evidence

ORD record
ord-d6f07a236e284cadb46c39551d525705
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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