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

HRID 1796637Notes

Reaction equation

HRID 1796637 reaction equation
[CH2:1]([O:3]C(C1C(OC)=C2C(NC3C=CC(OC4C=CC=CC=4)=CC=3)=C(C#N)C=NN2C=1)=O)C.[OH:33][C:34]([C:37]1[C:38](C)=[C:39]2[C:44]([NH:45][C:46]3[CH:51]=[CH:50][C:49]([O:52][C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)=[CH:48][CH:47]=3)=[C:43]([C:59]#[N:60])[CH:42]=[N:41][N:40]2[CH:61]=1)([CH3:36])[CH3:35].C(O)(C(F)(F)F)=O.O.C(O)(C(F)(F)F)=O.CC#N>>[OH:33][C:34]([C:37]1[C:38]([O:3][CH3:1])=[C:39]2[C:44]([NH:45][C:46]3[CH:47]=[CH:48][C:49]([O:52][C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)=[CH:50][CH:51]=3)=[C:43]([C:59]#[N:60])[CH:42]=[N:41][N:40]2[CH:61]=1)([CH3:36])[CH3:35]

Participants

5

Reactant 4

HCID 21924481TFA acetonitrileHCID 221796836-(1-Hydroxy-1-methyl-ethyl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrileHCID 22392675Trifluoroacetic acid waterHCID 693274533-Cyano-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester

Product 1

HCID 221794656-(1-Hydroxy-1-methyl-ethyl)-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrileYield 98%

Procedure

The title compound (170 mg, 98%) was prepared from 393 (180 mg, 0.42 mmol) by a route analogous to that used for the preparation of compound 396. It has a retention time of 6.49 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)+=413.3

Workup

  1. customtime 10 min

Sources & evidence

ORD record
ord-0717bce4404c4e199003e8028f9bc973
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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