Water → 3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-carbonyl-N-hydroxylmorpholinyl-acetamidine

HRID 1796660Notes

Reaction equation

HRID 1796660 reaction equation
[OH:1][NH:2][C:3]([N:5]1CCOCC1)=N.C[CH2:12][N:13](C(C)C)C(C)C.[C:20]([C:22]1[CH:27]=[N:26][N:25]2[CH:28]=[C:29]([C:32](Cl)=[O:33])[C:30]([CH3:31])=[C:24]2[C:23]=1[NH:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:38][CH:37]=1)#[N:21].O.[CH3:50][CH2:51][O:52][C:53]([CH3:55])=O>CN(C=O)C>[C:20]([C:22]1[CH:27]=[N:26][N:25]2[CH:28]=[C:29]([C:32]([CH:12]([N:13]3[CH2:55][CH2:53][O:52][CH2:51][CH2:50]3)[C:3]([NH:2][OH:1])=[NH:5])=[O:33])[C:30]([CH3:31])=[C:24]2[C:23]=1[NH:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:38][CH:37]=1)#[N:21]

Participants

7

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 221796093-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carbonyl chlorideHCID 178513433HCID 178513433, compound

Product 1

HCID 1784290863-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-carbonyl-N-hydroxylmorpholinyl-acetamidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-hydroxy-morpholine-4-carboxamidine (Example 419A) (20.2 mg, 0.13 mmol) and Hunig's base (45 μl, 0.26 mmol) in DMF (1 ml) at −5° C. was added a solution of 3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carbonyl chloride (Example 412B) (51 mg, 0.12 mmol) in DMF (1 ml) via syringe. The reaction mixture was warmed to rt, after 20 min, diluted with EtOAc, poured into water (50 ml), extracted with EtOAc (2×50 ml). The combined extracts were dried with Na2SO4, concentrated in vacuo and purified by prep. TLC to give the title compound (23 mg, 37%) (5% MeOH—CHCl3). It has a retention time of 5.79 min (standard LC1 method, 8 min run). LCMS Found: (M+H)+=512.2.

Workup

  1. extractionextracted with EtOAc (2×50 ml)
  2. dry with materialThe combined extracts were dried with Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by prep

Sources & evidence

ORD record
ord-6a20af5a3092424689cd646fc8512e16
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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