Diisopropylethylamine → 1-[(2'-Oxo-1',2',5,7-tetrahydro-1H-spiro[indeno[5,6-d]imidazole-6,3'-pyrrolo[2,3-b]pyridin]-2-yl)methyl]-4H-imidazo[1,5,4-de]quinoxaline-2,5(1H,6H)-dione

HRID 551105

Reaktionsgleichung

Reaktionsgleichung von HRID 551105
[NH2:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][C:19]=1[N+:20]([O-])=O)[CH2:16][C@:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2.[O:23]=[C:24]1[N:28]2[CH2:29][C:30](=[O:36])[NH:31][C:32]3[CH:33]=[CH:34][CH:35]=[C:26]([C:27]=32)[N:25]1[CH2:37][C:38]([O-])=O.[Na+].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C.CC(O)=O>[O:15]=[C:7]1[NH:8][C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:14]2[C:6]21[CH2:5][C:4]1[C:17](=[CH:18][C:19]3[N:20]=[C:38]([CH2:37][N:25]4[C:26]5[C:27]6[N:28]([CH2:29][C:30](=[O:36])[NH:31][C:32]=6[CH:33]=[CH:34][CH:35]=5)[C:24]4=[O:23])[NH:1][C:2]=3[CH:3]=1)[CH2:16]2

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66636782Sodium (2,5-dioxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetate2×HCID 67174155(S)-5-Amino-6-nitro-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2×

Produkt 1

HCID 235819531-[(2'-Oxo-1',2',5,7-tetrahydro-1H-spiro[indeno[5,6-d]imidazole-6,3'-pyrrolo[2,3-b]pyridin]-2-yl)methyl]-4H-imidazo[1,5,4-de]quinoxaline-2,5(1H,6H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 5,6-diamino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (30 mg, 0.11 mmol, described in Intermediate 13), sodium (2,5-dioxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetate (27 mg, 0.10 mmol, described in Intermediate 26), BOP (50 mg, 0.11 mmol), and N,N-diisopropylethylamine (0.019 mL, 0.11 mmol) was stirred in DMF (0.4 mL) at ambient temperature for 2 h, then AcOH (0.4 mL) was added and the resulting mixture was heated to 60° C. for 18 h. The mixture was allowed to cool and the precipitate was isolated by filtration. This solid was washed with H2O, then MeOH, then CH2Cl2, then dried in vacuo to give the title compound. MS: m/z=478 (M+1). HRMS: m/z=478.1606; calculated m/z=478.1622 for C26H20N7O3.

Aufarbeitung

  1. temperatureto cool
  2. customthe precipitate was isolated by filtration
  3. washThis solid was washed with H2O
  4. dry with materialMeOH, then CH2Cl2, then dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b2e14a3f612440a3a82b8b71086356db
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947677B2

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