1-Methylpiperazine → HCID 22179642, compound

HRID 1796651Notes

Reaction equation

HRID 1796651 reaction equation
[CH:1]([C:3]1[C:4]([CH3:28])=[C:5]2[C:10]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)=[C:9]([C:25]#[N:26])[CH:8]=[N:7][N:6]2[CH:27]=1)=O.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:28][C:4]1[C:3]([CH2:1][N:33]2[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]2)=[CH:27][N:6]2[C:5]=1[C:10]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:14][CH:13]=1)=[C:9]([C:25]#[N:26])[CH:8]=[N:7]2

Participants

6

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 22179494HCID 22179494, compound

Product 1

HCID 22179642HCID 22179642, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-formyl-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile (Example 8) (27 mg, 0.073 mmol) and 1-methyl-piperazine (8.1 μl, 0.073 mmol) in CH2Cl2 (2.5 ml) was stirred for 48 h, then treated with NaBH(OAc)3 (46.4 mg, 0.2 mmol) and stirred for 24 h. The mixture was diluted with CHCl3, washed with saturated NaHCO3 and H2O, dried with Na2SO4. Concentrated in vacuo and purified by prep. TLC to give the title compound (22 mg, 66%) (20% MeOH—CHCl3). It has a retention time of 4.90 min (standard LCl method, 8 min run). LCMS Found: (M+H)+=453.1

Workup

  1. stirringstirred for 24 h
  2. washwashed with saturated NaHCO3 and H2O
  3. dry with materialdried with Na2SO4
  4. concentrationConcentrated in vacuo
  5. custompurified by prep

Sources & evidence

ORD record
ord-70729b68717a4ef6bdb16a3776edd9cd
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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