Diisopropylethylamine → 6-bromo-4-(((1R)-2-fluoro-1,2-dimethylpropyl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 1507912Notes

Reaction equation

HRID 1507912 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](Cl)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1.Cl.[F:16][C:17]([CH3:22])([CH3:21])[C@H:18]([NH2:20])[CH3:19].FC(C)(C)[C@H](NC1C2N(C=CC=2)N=CC=1C(N)=O)C.C(N(C(C)C)CC)(C)C>CN1C(=O)CCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:20][C@H:18]([CH3:19])[C:17]([F:16])([CH3:22])[CH3:21])=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamideHCID 683494474-(((1R)-2-fluoro-1,2-dimethylpropyl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamideHCID 86677913(2R)-3-fluoro-3-methylbutan-2-amine hydrochloride

Product 1

HCID 683495236-bromo-4-(((1R)-2-fluoro-1,2-dimethylpropyl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 519 mg, 1.89 mmol), (R)-2-fluoro-1,2-dimethyl-propylamine hydrochloride salt (402 mg, 2.84 mmol, from Intermediate 2, step 3), and diisopropylethylamine (0.99 mL, 5.68 mmol) in NMP (2.0 mL) was heated to 100° C. for 1 hour in the CEM microwave. The mixture was cooled to rt, diluted with water and the resulting precipitate then filtered and allowed to air dry. This afforded 595 mg (92%) of a pale white solid as the title compound. HPLC (condition B): retention time=3.67 min. LCMS (condition B): m/z 343.1, 345.1. 1H NMR (500 MHz, CD3OD) δ ppm 8.16 (1 H, s), 7.67 (1 H, d, J=1.66 Hz), 7.04 (1 H, d, J=1.39 Hz), 4.11-4.60 (1 H, m), 1.45-1.54 (6 H, m), 1.43 (3 H, d, J=6.66 Hz).

Workup

  1. filtrationthe resulting precipitate then filtered
  2. customto air dry

Sources & evidence

ORD record
ord-c8a665d12bd34336bf37e7478dc2ffc1
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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