4-Chloropyrrolo[1,2-b]pyridazine-3-carboxamide → 4-[(2,2-Dimethyl-3-oxocyclopentyl)amino]pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 1408935Notes

Reaction equation

HRID 1408935 reaction equation
Cl[C:2]1[C:3]2[N:4]([CH:11]=[CH:12][CH:13]=2)[N:5]=[CH:6][C:7]=1[C:8]([NH2:10])=[O:9].[NH2:14][CH:15]1[CH2:19][CH2:18][C:17](=[O:20])[C:16]1([CH3:22])[CH3:21]>>[CH3:21][C:16]1([CH3:22])[C:17](=[O:20])[CH2:18][CH2:19][CH:15]1[NH:14][C:2]1[C:3]2[N:4]([CH:11]=[CH:12][CH:13]=2)[N:5]=[CH:6][C:7]=1[C:8]([NH2:10])=[O:9]

Participants

3

Reactant 2

HCID 679656194-Chloropyrrolo[1,2-b]pyridazine-3-carboxamideHCID 682916003-Amino-2,2-dimethylcyclopentanone

Product 1

HCID 683586194-[(2,2-Dimethyl-3-oxocyclopentyl)amino]pyrrolo[1,2-b]pyridazine-3-carboxamideYield 18.5%

Procedure

According to the procedure described in Example 1, 4-chloropyrrolo[1,2-b]-pyridazine-3-carboxamide (100 mg, 0.511 mmol, from Preparation 3) was reacted crude 3-amino-2,2-dimethylcyclopentanone (195 mg, from Step 2). Purification with reverse phase HPLC (Sunfire S10 30×250 mm column), eluting with 30 to 100% solvent B (10% methanol-90% water-0.1% TFA) in solvent A (90% methanol-10% water-0.1% TFA), gave the title compound (27 mg, 18% yield). 1H NMR (400 MHz, methanol-d4) δ ppm 8.15 (1 H, s), 7.50-7.70 (1 H, m), 6.86-7.37 (1 H, m), 6.47-6.90 (1 H, m), 4.49-4.78 (1 H, m), 2.18-2.70 (3 H, m), 1.75-2.26 (1 H, m), 1.03-1.17 (6 H, m); MS (ES+) m/z: 287.2 (M+H); HPLC retention time: 2.487 min (analytical HPLC Method A).

Workup

  1. customPurification with reverse phase HPLC (Sunfire S10 30×250 mm column)
  2. washeluting with 30 to 100% solvent B (10% methanol-90% water-0.1% TFA) in solvent A (90% methanol-10% water-0.1% TFA)

Sources & evidence

ORD record
ord-e1b3e0615bea48bb8e7bcd6102b099ab
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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