Methanol → tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzoate

HRID 718618Notes

Reaction equation

HRID 718618 reaction equation
[CH:1]([C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:9][CH:8]=[N:7][N:6]2[C:17]=1[C:18]1[CH:30]=[CH:29][C:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:20][CH:19]=1)=[O:2].O1CCOCC1.CO.[BH4-].[Na+]>O>[OH:2][CH2:1][C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:9][CH:8]=[N:7][N:6]2[C:17]=1[C:18]1[CH:30]=[CH:29][C:21]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 312751,4-DioxaneHCID 4311764Sodium borohydrideHCID 117732456tert-Butyl 4-(2-formyl-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzoate

Product 1

HCID 117732488tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 5f (315 mg, 0.772 mmol) was placed in a 40 mL vial equipped with a stir bar and then dioxane (10 mL) and MeOH (10 mL) were added. NaBH4 (51.0 mg, 1.35 mmol) was added and then the reaction was stirred at rt for 18 h. The reaction was diluted with water (20 mL) and the mixture was extracted with DCM (3×25 mL). The organic extracts were combined, dried over Na2SO4, and filtered. The solvent was removed under reduced pressure to afford compound 34a. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.09-8.17 (m, 2H), 8.06 (d, J=5.6 Hz, 1H), 7.75-7.86 (m, 2H), 6.15 (d, J=5.6 Hz, 1H), 4.86 (d, J=5.6 Hz, 2H), 3.87-4.05 (m, 8H), 2.52 (t, J=5.6 Hz, 1H), 1.61 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C22H26N4O4: 411.2 (M+H). Found: 411.4.

Workup

  1. customvial equipped with a stir bar
  2. extractionthe mixture was extracted with DCM (3×25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-64662ef93a544bfb9359612b05f79f53
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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