Methanol → HCID 68291726, compound

HRID 1507942Notes

Reaction equation

HRID 1507942 reaction equation
[CH:1]1([CH:4]([NH2:6])[CH3:5])[CH2:3][CH2:2]1.[Br:7][C:8]1[CH:9]=[C:10]2[C:15](Cl)=[C:14]([C:17]([NH2:19])=[O:18])[CH:13]=[N:12][N:11]2[CH:20]=1.CO>CN1C(=O)CCC1>[Br:7][C:8]1[CH:9]=[C:10]2[C:15]([NH:6][CH:4]([CH:1]3[CH2:3][CH2:2]3)[CH3:5])=[C:14]([C:17]([NH2:19])=[O:18])[CH:13]=[N:12][N:11]2[CH:20]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5192391-CyclopropylethanamineHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 68291726HCID 68291726, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-Cyclopropylethanamine (93 mg, 1.09 mmol) and 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 100 mg, 0.36 mmol) in NMP (0.5 mL) were heated in the CEM microwave at 120° C. for 10 min. The reaction was allowed to cool to room temperature before the addition of MeOH. The resulting precipitate was then filtered and air dried to afford the title compound (72 mg, 61%). HPLC (condition G): retention time=3.87 min. LCMS (condition B): m/z 323.0, 325.0. 1H NMR (500 MHz, MeOD) δ ppm 8.69 (1 H, d, J=4.99 Hz), 8.40-8.49 (2 H, m), 8.32-8.40 (1 H, m), 8.28 (1 H, s), 7.76 (1 H, td, J=6.59, 1.25 Hz), 7.68 (1 H, d, J=1.94 Hz), 4.12 (1 H, quin, J=6.45 Hz), 1.52 (3 H, d, J=6.38 Hz), 1.14-1.29 (1 H, m), 0.58-0.75 (2 H, m), 0.35-0.51 (2 H, m).

Workup

  1. filtrationThe resulting precipitate was then filtered
  2. customair dried

Sources & evidence

ORD record
ord-3b3355486a0f4446b7022ebf23582fae
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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