Diisopropylethylamine → HCID 68292021, compound

HRID 1507944Notes

Reaction equation

HRID 1507944 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.[NH2:16][CH2:17][C:18]1([CH2:21][OH:22])[CH2:20][CH2:19]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:16][CH2:17][C:18]3([CH2:21][OH:22])[CH2:20][CH2:19]3)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamideHCID 86706849HCID 86706849, compound

Product 1

HCID 68292021HCID 68292021, compoundYield 74%

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, 45 mg, 0.164 mmol), (1-(aminomethyl)cyclopropyl)methanol HCl salt (25.9 mg, 0.189 mmol) and DIPEA (0.072 mL, 0.410 mmol) in NMP (0.5 mL) was heated to 110° C. for 1 hr. The reaction mixture was purified on preparative HPLC to afford the title compound (41 mg, 74%). HPLC (condition G): retention time=2.73 min. LCMS (condition B): m/z 339.1, 341.1.

Workup

  1. customThe reaction mixture was purified on preparative HPLC

Sources & evidence

ORD record
ord-22d27c59df464b31905959872647ac10
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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