p-Toluenesulfonic acid → 5-(5-Amino-4-(piperidin-4-ylmethylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile

HRID 384631Notes

Reaction equation

HRID 384631 reaction equation
[NH2:1][C:2]1[C:3]([NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)=[CH:4][C:5]([NH:8][C:9]2[CH:14]=[N:13][C:12]([C:15]#[N:16])=[CH:11][N:10]=2)=[N:6][CH:7]=1.CC1C=CC(S(O)(=O)=O)=CC=1>>[NH2:1][C:2]1[C:3]([NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:4][C:5]([NH:8][C:9]2[N:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59613544Tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 426100465-(5-Amino-4-(piperidin-4-ylmethylamino)pyridin-2-ylamino)pyrazine-2-carbonitrileYield 6.2%

Procedure

Crude tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (50 mg) was loaded onto a MP-TsOH SPE cartridge, then eluted after 20 minutes with 2 M ammonia in methanol. The basic fractions were concentrated. Preparative HPLC gave 5-(5-amino-4-(piperidin-4-ylmethylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile (2.36 mg, 2.4% over 3 steps).

Workup

  1. washeluted after 20 minutes with 2 M ammonia in methanol
  2. concentrationThe basic fractions were concentrated

Sources & evidence

ORD record
ord-5f8d0786415641c5b016abef8e7b4d12
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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