TFA acetonitrile → 6-Hydroxy-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

HRID 1796638Notes

Reaction equation

HRID 1796638 reaction equation
[OH:1][C:2]1[C:3](C)=[C:4]2[C:9]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[C:8]([C:24]#[N:25])[CH:7]=[N:6][N:5]2[CH:26]=1.[C:28](O)(C(F)(F)F)=[O:29].O.C(O)(C(F)(F)F)=O.CC#N>>[OH:1][C:2]1[C:3]([O:29][CH3:28])=[C:4]2[C:9]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:13][CH:12]=3)=[C:8]([C:24]#[N:25])[CH:7]=[N:6][N:5]2[CH:26]=1

Participants

4

Reactant 3

HCID 21924481TFA acetonitrileHCID 221796716-Hydroxy-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrileHCID 22392675Trifluoroacetic acid water

Product 1

HCID 221796556-Hydroxy-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrileYield 76%

Procedure

The title compound (26 mg, 76%) was prepared from Example 398 (38 mg, 0.092 mmol) by a route analogous to that used for the preparation of compound 397A. It has a retention time of 6.08 min. (Column: HTS, 5 u, 4.6×50 mm; Gradient: 5-100% B in 8.0 min; A=0.1% TFA/H2O; B=0.1% TFA/CH3CN; Run time 10 min; Det: 215 nM; FR: 1.2 ml/min); MS Found: (M+H)+=373.2

Workup

  1. customtime 10 min

Sources & evidence

ORD record
ord-27bd8dbf02b546d5b7192f0eb7111b35
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

Loading…