1-(4-((1-(tert-Butoxycarbonyl)piperidin-3-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)pyridin-3-yl)-1H-pyrrole-3-carboxylic acid → 1-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-3-ylmethylamino)pyridin-3-yl)-1H-pyrrole-3-carboxylic acid

HRID 556828Notes

Reaction equation

HRID 556828 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]2[CH:21]=[C:20]([NH:22][C:23]3[CH:28]=[N:27][C:26]([C:29]#[N:30])=[CH:25][N:24]=3)[N:19]=[CH:18][C:17]=2[N:31]2[CH:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[CH:32]2)[CH2:9]1)=O)(C)(C)C>CO>[C:29]([C:26]1[N:27]=[CH:28][C:23]([NH:22][C:20]2[N:19]=[CH:18][C:17]([N:31]3[CH:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[CH:32]3)=[C:16]([NH:15][CH2:14][CH:10]3[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]3)[CH:21]=2)=[N:24][CH:25]=1)#[N:30]

Participants

3

Reactant 1

HCID 667465061-(4-((1-(tert-Butoxycarbonyl)piperidin-3-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)pyridin-3-yl)-1H-pyrrole-3-carboxylic acid

Product 1

HCID 596135191-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-3-ylmethylamino)pyridin-3-yl)-1H-pyrrole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4-((1-(tert-Butoxycarbonyl)piperidin-3-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)pyridin-3-yl)-1H-pyrrole-3-carboxylic acid (7 mg, 0.013 mmol) was dissolved in methanol (1 mL) and absorbed onto a TsOH solid phase extraction cartridge cartridge. After 1.5 h the cartridge was eluted with 7M ammonia in methanol. The eluent was evaporated to dryness to give 1-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-3-ylmethylamino)pyridin-3-yl)-1H-pyrrole-3-carboxylic acid.

Workup

  1. customabsorbed onto a TsOH solid phase extraction cartridge cartridge
  2. washAfter 1.5 h the cartridge was eluted with 7M ammonia in methanol
  3. customThe eluent was evaporated to dryness

Sources & evidence

ORD record
ord-5bf8163d0d5f4af4a6b46919a159d5fa
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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