HCID 10308281, compound → HCID 178515481, compound

HRID 1179129Notes

Reaction equation

HRID 1179129 reaction equation
[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]4[C:19]=3[CH:18]=[CH:17][C:16]([O:20]C)=[N:15]4)[CH:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1>N1CCOCC1>[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]4[C:19]=3[CH:18]=[CH:17][C:16]([OH:20])=[N:15]4)[CH:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 10308281HCID 10308281, compound

Product 1

HCID 178515481HCID 178515481, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8083MorpholineSolvent

Procedure

A solution of N-cyclopropyl-4-(6-methoxypyrazolo[1,5-b]pyridazin-3-yl)-2-pyrimidinamine (510 mg, 1.81 mmol) in morpholine (15 mL) was heated at an oil bath temperature of 130° C. for about 16 hours. The reaction mixture was cooled and the solvent removed in vacuo. The residue was disolved in CH2Cl2 and triturated with diethylether to give the title compound as a yellow solid (400 mg, 82%). 1H-NMR (300 MHz, d6-DMSO) δ 8.96 (d, 1H, J=9.7 Hz), 8.49 (s, 1H), 8.23 (d, 1H, J=5.0 Hz), 7.35 (s, 1H), 7.06 (d, 1H, J=5.1 Hz), 6.97 (d, 1H, J=9.5 Hz), 2.74 (m, 1H), 0.73 (m, 2H), 0.49 (bs, 2H); MS (ESI) (M+H)+ 269.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent removed in vacuo
  3. customtriturated with diethylether

Sources & evidence

ORD record
ord-27078e74746a447f96449c9888b61e0f
Source dataset
uspto-grants-2007_10
Patent number
US07279473B2

Reaction notes

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