p-Toluenesulfonic acid → N-(6-((5-Cyanopyrazin-2-yl)amino)-4-((piperidin-4-ylmethyl)amino)pyridin-3-yl)acetamide

HRID 384633Notes

Reaction equation

HRID 384633 reaction equation
C(N(CC)CC)C.C(O[C:12](=[O:14])[CH3:13])(=O)C.[NH2:15][C:16]1[C:17]([NH:31][CH2:32][CH:33]2[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]2)=[CH:18][C:19]([NH:22][C:23]2[CH:28]=[N:27][C:26]([C:29]#[N:30])=[CH:25][N:24]=2)=[N:20][CH:21]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C>[C:29]([C:26]1[N:27]=[CH:28][C:23]([NH:22][C:19]2[N:20]=[CH:21][C:16]([NH:15][C:12](=[O:14])[CH3:13])=[C:17]([NH:31][CH2:32][CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[CH:18]=2)=[N:24][CH:25]=1)#[N:30]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59613544Tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 42610172N-(6-((5-Cyanopyrazin-2-yl)amino)-4-((piperidin-4-ylmethyl)amino)pyridin-3-yl)acetamideYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (11 μL, 0.082 mmol) and acetic anhydride (8 μL, 0.082 mmol) were added to a solution of tert-butyl 4-((5-amino-2-(5-cyanopyrazin-2-ylamino)-pyridin-4-ylamino)-methyl)-piperidine-1-carboxylate (29 mg, 0.068 mmol) in DMF (1 mL) at 0° C. After 2 hours, the mixture was loaded onto a MP-TsOH SPE cartridge, and eluted with 2M ammonia in methanol. The basic fractions were combined and concentrated. Purified by preparative HPLC gave N-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-4-ylmethylamino)pyridin-3-yl)acetamide (7.4 mg, 32%).

Workup

  1. washeluted with 2M ammonia in methanol
  2. concentrationconcentrated
  3. customPurified by preparative HPLC

Sources & evidence

ORD record
ord-58b3d60dab5c47c0beb5036e596be19f
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

Loading…