Benzylamine → HCID 22179730, compound

HRID 1796654Notes

Reaction equation

HRID 1796654 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]([C:11]1[C:12]([CH3:36])=[C:13]2[C:18]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:22][CH:21]=3)=[C:17]([C:33]#[N:34])[CH:16]=[N:15][N:14]2[CH:35]=1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CN(C=O)C.C(Cl)(Cl)Cl>[CH2:1]([NH:8][CH2:9][C:11]1[C:12]([CH3:36])=[C:13]2[C:18]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:24][CH:25]=3)=[C:17]([C:33]#[N:34])[CH:16]=[N:15][N:14]2[CH:35]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22179494HCID 22179494, compound

Product 1

HCID 22179730HCID 22179730, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Benzylamine (10 μl, 0.09 mmol) was added to a solution of 6-formyl-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile (Example 8) (32 mg, 0.087 mmol) in CH2Cl2/DMF (10/1) (2.2 ml). The mixture was stirred overnight, then treated with NaBH(OAc)3 (55 mg, 0.26 mmol) and stirred overnight again. 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 (28 mg, 70%) as yellow-green oil (10% MeOH—CHCl3). It has a retention time of 6.46 min (standard LCl method, 8 min run). LCMS Found: (M+H)+=460.20

Workup

  1. stirringstirred overnight again
  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-3f257c300d5542c289e2aec0c2574053
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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