Triethylamine → HCID 42610483, compound

HRID 384626Notes

Reaction equation

HRID 384626 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)[CH:3]=1.[NH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]1.C(N(CC)CC)C>CN1CCCC1=O>[NH:22]1[CH2:23][CH2:24][CH:19]([CH2:18][NH:17][C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[N:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=3)[CH:3]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 56926364HCID 56926364, compound

Product 1

HCID 42610483HCID 42610483, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 5-(6-chloropyrimidin-4-ylamino)pyrazine-2-carbonitrile (124 mg, 0.533 mmol), tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (228 mg, 1.066 mmol) and triethylamine (150 μL, 1.07 mmol) in 1-methyl-2-pyrrolidinone (1 mL) was heated at 145° C. for 15 minutes using microwave irradiation. The mixture was concentrated in vacuo and the residue purified by preparative HPLC. The purified solid was dissolved in dichloromethane (2 mL) and trifluoroacetic acid (3 mL) and was stirred for 1 hour at room temperature before being applied to a MP-TsOH cartridge. After washing with methanol, the pure product was eluted using 7M ammonia to give 5-(6-(piperidin-4-ylmethylamino)pyrimidin-4-ylamino)pyrazine-2-carbonitrile (10.3 mg, 6%).

Workup

  1. custommicrowave irradiation
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue purified by preparative HPLC
  4. dissolutionThe purified solid was dissolved in dichloromethane (2 mL)
  5. washAfter washing with methanol
  6. washthe pure product was eluted

Sources & evidence

ORD record
ord-71bf0e3b3266405094a6cc0502deb1a5
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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