Trifluoroacetic acid → N-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-4-ylmethoxy)pyridin-3-yl)-2-(dimethylamino)acetamide

HRID 384654Notes

Reaction equation

HRID 384654 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[C:13]([NH:31][C:32](=[O:37])[CH2:33][N:34]([CH3:36])[CH3:35])=[CH:12][N:11]=2)=[N:7][CH:8]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10]2[N:11]=[CH:12][C:13]([NH:31][C:32](=[O:37])[CH2:33][N:34]([CH3:35])[CH3:36])=[C:14]([O:16][CH2:17][CH:18]3[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]3)[CH:15]=2)=[N:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59613336Tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(2-(dimethylamino)acetamido)pyridin-4-yloxy)methyl)piperidine-1-carboxylate

Product 1

HCID 42610358N-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-4-ylmethoxy)pyridin-3-yl)-2-(dimethylamino)acetamideYield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-((2-(5-cyanopyrazin-2-ylamino)-5-(2-(dimethylamino)acetamido) pyridin-4-yloxy)methyl)piperidine-1-carboxylate (24 mg, 0.047 mmol) and trifluoroacetic acid (2 mL) in dichloromethane (10 mL) was stirred for 45 minutes. The solution was concentrated and the residue was loaded onto a MP-TsOH SPE cartridge. Elution with 2M ammonia in methanol gave N-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-4-ylmethoxy)pyridin-3-yl)-2-(dimethylamino)acetamide as a yellow solid (14 mg, 72%).

Workup

  1. concentrationThe solution was concentrated
  2. washElution with 2M ammonia in methanol

Sources & evidence

ORD record
ord-bb61d3ff11b34cb39880630fdb1b0e68
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

Loading…