Acetic Acid → HCID 66712082, Verbindung

HRID 1262135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1262135
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:24]2[C:19]([CH:20]=[N:21][C:22]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([CH:32]4[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]4)=[CH:28][C:27]=3[O:38][CH3:39])=[N:23]2)=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>O1CCCC1>[NH:3]1[CH:4]=[CH:5][N:1]=[C:2]1[CH2:6][N:35]1[CH2:34][CH2:33][CH:32]([C:29]2[CH:30]=[CH:31][C:26]([NH:25][C:22]3[N:21]=[CH:20][C:19]4=[CH:18][CH:17]=[C:16]([C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=5[O:9][CH3:8])[N:24]4[N:23]=3)=[C:27]([O:38][CH3:39])[CH:28]=2)[CH2:37][CH2:36]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 249551H-imidazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66711490HCID 66711490, Verbindung

Produkt 1

HCID 66712082HCID 66712082, VerbindungAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Imidazole-2-carboxaldehyde (0.011 g, 0.112 mmol) and [7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(2-methoxy-4-piperidin-4-yl-phenyl)-amine (53 mg, 0.12 mmol) were treated with sodium triacetoxyborohydride (0.033 g, 0.157 mmol) and acetic acid (0.064 mL, 0.112 mmol) in tetrahydrofuran (0.900 mL) at room temperature overnight. The reaction mixture was then concentrated and partitioned between dichloromethane and a saturated aqueous sodium bicarbonate solution. It was dried on NaSO4, filtered and concentrated. The product was isolated by reverse phase hplc (Gilson) to afford {4-[1-(1H-imidazol-2-ylmethyl)-piperidin-4-yl]-2-methoxy-phenyl}-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine as a yellow foam (5 mg, 9%). 1H-NMR (CDCl3) δ 9.63 (s, 1H), 8.69 (s, 1H), 8.29 (d, J=8.7 Hz, 1H), 8.00 (d, J=6.2 Hz, 1H), 7.44 (m, 2H), 7.13 (m, 1H), 7.07 (d, J=8.3 Hz, 1H), 7.02 (s, 2H), 6.83 (d, J=4.7 Hz, 1H), 6.73 (m, 2H), 3.89 (s, 3H), 3.84 (s, 3H), 3.71 (s, 2H), 2.97 (d, J=11.4 Hz, 2H), 2.49 (m, 1H), 2.25 (m, 2H), 1.85 (m, 5H); LC/MS (ESI+): 510.2 (M+H).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned between dichloromethane
  3. customIt was dried on NaSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was isolated by reverse phase hplc (Gilson)

Quellen und Nachweise

ORD-Eintrag
ord-bc58d3fb56b54c8e8d91b0d8a4e2f430
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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