Aluminium lithium hydride → HCID 68292166, compound

HRID 1507987Notes

Reaction equation

HRID 1507987 reaction equation
[C:1]([C:3]([CH3:28])([CH3:27])[C@H:4]([NH:6][C:7]1[C:8]2[N:9]([CH:16]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[CH:18]=2)[N:10]=[CH:11][C:12]=1[C:13]([NH2:15])=[O:14])[CH3:5])#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:2][CH2:1][C:3]([CH3:27])([CH3:28])[C@H:4]([NH:6][C:7]1[C:8]2[N:9]([CH:16]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[CH:18]=2)[N:10]=[CH:11][C:12]=1[C:13]([NH2:15])=[O:14])[CH3:5]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68292193HCID 68292193, compound

Product 1

HCID 68292166HCID 68292166, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (R)-4-((3-cyano-3-methylbutan-2-yl)amino)-6-(6-methoxypyridin-3-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide (120 mg, 0.317 mmol) taken in THF (20 mL) under nitrogen atmosphere was added LAH (1M solution in THF) (12 mL, 12.00 mmol) at 0° C. slowly. The reaction mixture was stirred at 25° C. for overnight. Reaction was monitored by LCMS. Reaction mixture was quenched with saturated sodium sulfate and filtered through celite. The filtrate was taken and the two layers were separated. The organic layer was dried and concentrated under reduced pressure to get (R)-4-((4-amino-3,3-dimethylbutan-2-yl)amino)-6-(6-methoxypyridin-3-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide (100 mg, 0.261 mmol, 82% yield) as yellow colored semi solid. LCMS Purity: Column: Purospher@star RP-18 (4×55) mm, 3 μm. Buffer: 20 mM NH4OAc in water Mobile Phase A: Buffer: CH3CN (90:10). Solvent B: Buffer: CH3CN (10:90). Flow: 2.5 mL/min, Time: 0-0, 2-100, 2.5-100, 3.0-0 min. Retention Time: 1.173 min. Purity: 93.15% (m/z=383.2 M+1).

Workup

  1. customReaction
  2. customReaction mixture
  3. customwas quenched with saturated sodium sulfate
  4. filtrationfiltered through celite
  5. customthe two layers were separated
  6. customThe organic layer was dried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dadbd740e8b945dea08533c8919f3ce0
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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