Phosphorus oxychloride → 4-(2-(4-chloro-3-(4-fluorophenyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)ethyl)morpholine

HRID 1775582Notes

Reaction equation

HRID 1775582 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15](O)=[C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:13]=[N:12][C:11]=3[N:10]([CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[N:9]=2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:34]>>[Cl:34][C:15]1[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:13][N:12]=[C:11]2[N:10]([CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:16]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515334HCID 178515334, compound

Product 1

HCID 665761774-(2-(4-chloro-3-(4-fluorophenyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)ethyl)morpholine

Procedure

3-(4-fluorophenyl)-1-(2-morpholinoethyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-4-ol (27.8 mg, 0.07 mmol) was heated to 80° C. in POCl3 (0.5 ml) for 2.75 h the solvent was removed in vacuo and the crude purified by preparative HPLC to give Compound 78 as an orange solid (10.7 mg).

Workup

  1. customwas removed in vacuo
  2. customthe crude purified by preparative HPLC

Sources & evidence

ORD record
ord-595385f069154a3abbde7464ceb480bb
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

Loading…