Triethylamine → 3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methoxy-methyl-amide

HRID 1796657Notes

Reaction equation

HRID 1796657 reaction equation
[C:1]([C:3]1[CH:8]=[N:7][N:6]2[CH:9]=[C:10]([C:13](Cl)=[O:14])[C:11]([CH3:12])=[C:5]2[C:4]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)#[N:2].CCN(CC)CC.Cl.[CH3:38][O:39][NH:40][CH3:41]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:38][O:39][N:40]([CH3:41])[C:13]([C:10]1[C:11]([CH3:12])=[C:5]2[C:4]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)=[C:3]([C:1]#[N:2])[CH:8]=[N:7][N:6]2[CH:9]=1)=[O:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 221796093-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carbonyl chloride

Product 1

HCID 210250653-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methoxy-methyl-amideYield 71.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carbonyl chloride (Example 412B) (181 mg, 0.45 mmol) in CH2Cl2 (3 ml) was added Et3N (160 μl, 1.13 mmol) followed by O,N-dimethylhydroxyamine hydrochloride (44 mg, 0.45 mmol) in one portion. The mixture was stirred overnight, diluted with CHCl3 (20 ml), washed with water (2×20 ml), dried with Na2SO4. Concentrated in vacuo and purified by prep. TLC to give the title compound (138 mg, 72%) (50% EtOAc—hexanes). It has a retention time of 6.45 min (standard LCl method, 8 min run). LCMS Found: (M+H)+=428.1

Workup

  1. washwashed with water (2×20 ml)
  2. dry with materialdried with Na2SO4
  3. concentrationConcentrated in vacuo
  4. custompurified by prep

Sources & evidence

ORD record
ord-09d85597fb8a49d39c9d5e5078f6e3ee
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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