Benzylamine → HCID 59331717, compound

HRID 1255844Notes

Reaction equation

HRID 1255844 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:26])[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[CH:14]=[CH:15][CH:16]=2)[CH3:10])[CH:5]=[N:4][CH:3]=1.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.CO.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH2:27]([NH:34][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:26])[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[CH:14]=[CH:15][CH:16]=2)[CH3:10])[CH:5]=[N:4][CH:3]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 3

HCID 7504BenzylamineHCID 23676156Sodium t-butoxideHCID 25218459HCID 25218459, compound

Product 1

HCID 59331717HCID 59331717, compoundYield 20%

Reagents, catalysts & solvents 4

HCID 178418851HCID 178418851, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (S)—N-(3-(1-(6-chloropyrazin-2-ylamino)ethyl)phenyl)-3-methylbenzamide (55 mg, 0.15 mmol), benzylamine (0.033 mL, 0.3 mmol), bis(tri-t-butylphosphine)palladium(0) (8 mg, 0.015 mmol) and sodium tert-butoxide (22 mg, 0.225 mmol) in dry toluene (1 mL) was heated in a microwave reactor at 110° C. for 1 hour. After this time the mixture was allowed to cool to room temperature and was diluted with ethyl acetate (5 mL)/methanol (5 mL), filtered through Celite and concentrated under reduced pressure to give a yellow solid which was purified by flash chromatography (silica, ethyl acetate/hexanes) followed by passage through a column of Sephadex with methanol as eluant to give the (S)—N-(3-(1-(6-(benzylamino)pyrazin-2-ylamino)ethyl)phenyl)-3-methylbenzamide (13 mg, 20%) as an unstable blue oil.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through Celite
  3. concentrationconcentrated under reduced pressure
  4. customto give a yellow solid which
  5. customwas purified by flash chromatography (silica, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0060f43e07d24a97a1834bd2f8fa9bda
Source dataset
uspto-grants-2013_06
Patent number
US08461161B2

Reaction notes

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