Sodium borohydride → HCID 86707703, compound

HRID 1408946Notes

Reaction equation

HRID 1408946 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]=[C:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[C:18]3[N:19]([CH:26]=[C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:28]=3)[N:20]=[CH:21][C:22]=2[C:23]([NH2:25])=[O:24])[C:12]1([CH3:36])[CH3:35])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([NH:10][C@@H:11]1[CH2:15][CH2:14][C@H:13]([NH:16][C:17]2[C:18]3[N:19]([CH:26]=[C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:28]=3)[N:20]=[CH:21][C:22]=2[C:23]([NH2:25])=[O:24])[C:12]1([CH3:36])[CH3:35])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68292186HCID 68292186, compound

Product 1

HCID 86707703HCID 86707703, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (1.5 mg, 0.040 mmol) was added to a solution of 4-(3-(benzylimino)-2,2-dimethylcyclopentylamino)-6-phenylpyrrolo[1,2-b]pyridazine-3-carboxamide (6 mg, 0.013 mmol, from Step 1) in methanol (1 mL) at 0° C. After 30 min at 0° C., the mixture was quenched with saturated ammonium chloride (1 mL), diluted with ethyl acetate (60 mL), washed with water, brine, dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography, eluting with 0 to 10% methanol in dichloromethane, to give the title compound (4.0 mg, 60% yield). 1H NMR (400 MHz, methanol-d4) δ ppm 8.13 (1 H, s), 7.91 (1 H, d, J=1.54 Hz), 7.56-7.84 (2 H, m), 7.04-7.53 (9 H, m), 4.32 (1 H, t, J=8.91 Hz), 3.69-4.04 (2 H, m), 2.77-2.95 (1 H, m), 2.08-2.52 (2 H, m), 1.43-1.81 (2 H, m), 0.97-1.15 (6 H, m); MS (ES+) m/z: 454.4 (M+H); HPLC retention time: 6.605 min (analytical HPLC Method L).

Workup

  1. customthe mixture was quenched with saturated ammonium chloride (1 mL)
  2. additiondiluted with ethyl acetate (60 mL)
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 0 to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-042d908fe52040aaa2a21d99258ae6f2
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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