Water → (R)-6-bromo-4-(1-cyclopropylethylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 1507917Notes

Reaction equation

HRID 1507917 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.[CH:16]1([C@H:19]([NH2:21])[CH3:20])[CH2:18][CH2:17]1.CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:21][C@@H:19]([CH:16]3[CH2:18][CH2:17]3)[CH3:20])=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 55219897(1R)-1-cyclopropylethan-1-amine hydrochlorideHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 68291753(R)-6-bromo-4-(1-cyclopropylethylamino)pyrrolo[1,2-b]pyridazine-3-carboxamideYield 82.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 500 mg, 1.821 mmol), (R)-1-cyclopropylethanamine HCl salt (277 mg, 2.277 mmol) and DIPEA (0.795 mL, 4.55 mmol) in NMP (5 mL) was heated to 100° C. for 4 hr. The reaction mixture was added 10 mL of water and stirred for 10 minutes. The solid was collected by vacuum filtration and dried to afford the title compound (485.4 mg, 79%). HPLC (condition G): retention time=2.29 min. LCMS (condition B): m/z 324.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.70 (1 H, d, J=8.1 Hz), 8.22 (1 H, s), 7.84 (1 H, d, J=1.8 Hz), 6.99 (1 H, d, J=1.8 Hz), 3.78-3.91 (1H, m), 1.29 (3 H, d, J=6.2 Hz), 0.99-1.11 (1 H, m), 0.42-0.53 (2 H, m), 0.33-0.40 (1H, m), 0.22-0.29 (1 H, m).

Workup

  1. filtrationThe solid was collected by vacuum filtration
  2. customdried

Sources & evidence

ORD record
ord-be8ed7078eb4415a98e347f9a46992b4
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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