tert-Butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-(3-(morpholinomethyl)-1H-pyrrol-1-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate → 5-(5-(3-(morpholinomethyl)-1H-pyrrol-1-yl)-4-(piperidin-3-ylmethylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile

HRID 384661Notes

Reaction equation

HRID 384661 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]3)[C:13]([N:31]3[CH:35]=[CH:34][C:33]([CH2:36][N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)=[CH:32]3)=[CH:12][N:11]=2)=[N:7][CH:8]=1)#[N:2]>CO>[O:40]1[CH2:41][CH2:42][N:37]([CH2:36][C:33]2[CH:34]=[CH:35][N:31]([C:13]3[C:14]([NH:16][CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]4)=[CH:15][C:10]([NH:9][C:6]4[N:7]=[CH:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=4)=[N:11][CH:12]=3)[CH:32]=2)[CH2:38][CH2:39]1

Participants

3

Reactant 1

HCID 66746356tert-Butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-(3-(morpholinomethyl)-1H-pyrrol-1-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 596133275-(5-(3-(morpholinomethyl)-1H-pyrrol-1-yl)-4-(piperidin-3-ylmethylamino)pyridin-2-ylamino)pyrazine-2-carbonitrileYield 7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude tert-butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-(3-(morpholinomethyl)-1H-pyrrol-1-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (90 mg) was dissolved in methanol (1 mL) and absorbed onto a TsOH solid phase extraction cartridge and allowed to stand for 2 h. The cartridge was eluted with 7M ammonia in methanol. The basic fractions were evaporated to dryness. The crude product was purified by HPLC to give 5-(5-(3-(morpholinomethyl)-1H-pyrrol-1-yl)-4-(piperidin-3-ylmethylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile (4.93 mg, 7% over 3 steps).

Workup

  1. customabsorbed onto a TsOH solid phase extraction cartridge
  2. washThe cartridge was eluted with 7M ammonia in methanol
  3. customThe basic fractions were evaporated to dryness
  4. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-aed0ead6bb2e45a8bd80801902528de9
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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