HCID 10308281, compound → HCID 178515481, compound

HRID 729347Notes

Reaction equation

HRID 729347 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-e54b99911a554bb6b01109b14516d0fb
Source dataset
uspto-grants-2009_09
Patent number
US07582630B2

Reaction notes

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