Benzophenone imine → N-(diphenylmethylene)-1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine

HRID 1969560Notes

Reaction equation

HRID 1969560 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH2:20][NH2:21])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[C:22]1([C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=N)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[C:22]1([C:28]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[N:21][CH2:20][C:18]2[N:19]=[C:14]3[CH:13]=[CH:12][N:11]([S:1]([C:4]4[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=4)(=[O:2])=[O:3])[C:15]3=[N:16][CH:17]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 136809Benzophenone imineHCID 58009892HCID 58009892, compound

Product 1

HCID 58557423N-(diphenylmethylene)-1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamineYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (2.00 g, 6.61 mmol, Example #5 Step C) in DCM (30 mL) was added diphenylmethanimine (1.16 mL, 6.61 mmol). After about 2 d, the reaction mixture was concd in vacuo to provide N-(diphenylmethylene)-1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (2.75 g, 89%) as a foam and used without further purification. LC/MS (Table 1, Method a) Rt=3.02 min; MS m/z: 467 (M+H)+.

Sources & evidence

ORD record
ord-f89ef2b6caa04c63bf19c9c66334a80b
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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