Sodium cyanoborohydride → HCID 68650796, compound

HRID 646716Notes

Reaction equation

HRID 646716 reaction equation
[NH2:1][C:2]1[C:3]([C:16]([NH:18][CH3:19])=[O:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=O)[CH:9]=2)=[CH:6][N:7]=1.[CH2:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1)[CH2:21][CH3:22].C([BH3-])#N.[Na+]>>[NH2:1][C:2]1[C:3]([C:16]([NH:18][CH3:19])=[O:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:28][CH2:27][C:26]3[CH:29]=[CH:30][C:23]([CH2:20][CH2:21][CH3:22])=[CH:24][CH:25]=3)[CH:9]=2)=[CH:6][N:7]=1

Participants

4

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 12162002(4-Propylphenyl)methanamineHCID 58710602HCID 58710602, compound

Product 1

HCID 68650796HCID 68650796, compoundYield 32.4%

Procedure

To a stirred solution of 3-amino-6-(3-formylphenyl)-N-methylpyrazine-2-carboxamide (50 mg, 0.19 mmol) and 4-propylbenzylamine (35.7 mg, 0.24 mmol) in TBF (5 mL) was added sodium cyanoborohydride (ca. 5 eq.) and the solution was stirred until refluxed for 1 h. The solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (50 mL) and saturated aqueous solution of Na2CO3 (10 mL). The phases were separated. The organic layer was washed with saturated aqueous sodium chloride then dried (Na2SO4). Filtration and concentration followed by HPLC purification gave (24 mg, 32% yield) of 3-amino-N-methyl-6-[3-({[(4-propylphenyl)methyl]amino}methyl)phenyl]pyrazine-2-carboxamide: 1H NMR (400 MHz; DMSO-d6): 9.7 (br s, 1H); 9.0 (m, 1H); 8.87 (s, 1H); 8.5 (s, 1H); 8.4 (d, 1H); 7.5 (m, 6H); 7.43 (m, 2H); 4.2 (d, 2H); 2.82 (d, 3H); 2.56 (m, 2H); 1.6 (m, 2H); 0.9 (m, 3H); MS (EI) for C23H27N5O: 390 (MH+).

Workup

  1. temperatureuntil refluxed for 1 h
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (50 mL) and saturated aqueous solution of Na2CO3 (10 mL)
  4. customThe phases were separated
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialthen dried (Na2SO4)
  7. filtrationFiltration and concentration
  8. customfollowed by HPLC purification

Sources & evidence

ORD record
ord-c5dbde9ed8a14eaa97b343f653352b31
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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