Sodium cyanoborohydride → HCID 68650966, Verbindung

HRID 646717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646717
[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.[NH2:20][CH:21]1[C:29]2[C:24](=[C:25]([F:31])[CH:26]=[CH:27][C:28]=2[F:30])[CH2:23][CH2:22]1.[C:32]([BH3-])#N.[Na+]>C1COCC1.C(O)(=O)C>[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:20][CH:21]3[C:29]4[C:24](=[C:25]([F:31])[CH:26]=[CH:27][C:28]=4[F:30])[CH:23]([CH3:32])[CH2:22]3)[CH:9]=2)=[CH:6][N:7]=1

Komponenten

6

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 584399044,7-Difluoro-2,3-dihydro-1H-inden-1-amineHCID 58710602HCID 58710602, Verbindung

Produkt 1

HCID 68650966HCID 68650966, VerbindungAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-amino-6-(3-formylphenyl)-N-methylpyrazine-2-carboxamide (50 mg, 0.19 mmol) and 1-amino-4,7-difluoroindane (67.6 mg, 0.4 mmol) in THF (5 mL) was added sodium cyanoborohydride (62.8 mg, 1 mmol) and 1 drop of acetic acid. The solution was stirred overnight and 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 HCl (5 mL 0.5 M) then saturated aqueous sodium chloride and dried (Na2SO4). Filtration and concentration follow by hplc purification gave (42.2 mg, 50% yield) of 3-amino-6-(3-{[(4,7-difluoro-3-methyl-2,3-dihydro-1H-inden-1-yl)amino]methyl}phenyl)-N-methylpyrazine-2-carboxamide. An excess of HCl in dioxane (0.2 mL, 4.0 M) was added to the solution and the solvent was removed to give hydrochloride: 1H NMR (400 MHz; DMSO-d6): 10.1 (br s, 1H); 9.7 (br s, 1H); 9.0 (m, 1H); 8.85 (s, 1H); 8.2 (m, 1H); 7.5 (m, 2H); 7.3-7.2 (m, 2H); 5.0 (m, 1H); 4.6-4.15 (m, 3H); 3.4 (m, 1H); 2.95 (m, 1H); 2.85 (d, 3H); 2.6 (m, 1H); 2.46 (m, 1H); MS (EI) for C22H21N50F2 HCl: 410 (MH+).

Aufarbeitung

  1. customsolvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate (50 mL) and saturated aqueous solution of Na2CO3 (10 mL)
  3. customThe phases were separated
  4. washThe organic layer was washed with HCl (5 mL 0.5 M)
  5. dry with materialsaturated aqueous sodium chloride and dried (Na2SO4)
  6. filtrationFiltration and concentration
  7. customfollow by hplc purification

Quellen und Nachweise

ORD-Eintrag
ord-b8b7715a2bf947d29063a24d04a0f8a7
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704995B2

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