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

HRID 1525446Notes

Reaction equation

HRID 1525446 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-4ad1d8ca9c48439c94cdadafcc6c1dad
Source dataset
uspto-grants-2015_07
Patent number
US09079909B2

Reaction notes

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