Acetic Acid → 2-((3-(2-Oxa-6-azaspiro[3.5]nonan-6-ylmethyl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 921819

Reaktionsgleichung

Reaktionsgleichung von HRID 921819
[Cl:1][C:2]1[C:7]([CH:8]=O)=[CH:6][C:5]([C:10]#[N:11])=[CH:4][C:3]=1[NH:12][C:13]1[N:18]=[C:17]([NH:19][CH:20]2[CH2:22][CH2:21]2)[C:16]2=[N:23][CH:24]=[C:25]([C:26]#[N:27])[N:15]2[N:14]=1.C(O)(=O)C.[CH2:32]1[C:35]2([CH2:40][CH2:39][CH2:38][NH:37][CH2:36]2)[CH2:34][O:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.ClCCCl>[CH2:32]1[C:35]2([CH2:40][CH2:39][CH2:38][N:37]([CH2:8][C:7]3[C:2]([Cl:1])=[C:3]([NH:12][C:13]4[N:18]=[C:17]([NH:19][CH:20]5[CH2:21][CH2:22]5)[C:16]5=[N:23][CH:24]=[C:25]([C:26]#[N:27])[N:15]5[N:14]=4)[CH:4]=[C:5]([C:10]#[N:11])[CH:6]=3)[CH2:36]2)[CH2:34][O:33]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 513419452-Oxa-6-azaspiro[3.5]nonaneHCID 867086482-((2-Chloro-5-cyano-3-formylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Produkt 1

HCID 899340582-((3-(2-Oxa-6-azaspiro[3.5]nonan-6-ylmethyl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of 2-((2-chloro-5-cyano-3-formylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 400) (20 mg, 0.053 mmol), acetic acid (9.07 tli, 0.158 mmol) and 2-oxa-6-azaspiro[3.5]nonane (16.79 mg, 0.132 mmol) in THF (0.5 ml) was stirred at room temperature to for 5 min. to achieve solution. DCE (0.5 mL) was added and after 25 min, sodium triacetoxyborohydride (33.6 mg, 0.158 mmol) was added. LCMS analysis found the desired mass of the product. The mixture was stirred overnight. The reaction mixture was then quenched with saturated aqueous NaHCO3 and stirred for 10 minutes. It was dried with a stream of nitrogen and then dissolved in DMF (1.5 mL) and purified by reverse-phase preparative LCMS.

Aufarbeitung

  1. stirringThe mixture was stirred overnight
  2. customThe reaction mixture was then quenched with saturated aqueous NaHCO3
  3. stirringstirred for 10 minutes
  4. customIt was dried with a stream of nitrogen
  5. dissolutiondissolved in DMF (1.5 mL)
  6. custompurified by reverse-phase preparative LCMS

Quellen und Nachweise

ORD-Eintrag
ord-9ff3a299ca2b43ebaac89b4420243370
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273057B2

Verknüpfte Notizen

Wird geladen…