Dimethylformamide → HCID 131720606, Verbindung

HRID 1599066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1599066
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([N:13](C(C)C)C2C=CC(OC)=CC=2)=[O:12])[C:6]2[CH:25]=[CH:26][CH:27]=[CH:28][C:5]=2[N:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:3]1=[O:35].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=2N=N1.[CH:63]1C=CC2N(O)N=N[C:67]=2[CH:68]=1.[NH:73]1[C:81]2[C:76](=[CH:77][CH:78]=[CH:79][CH:80]=2)[CH:75]=[C:74]1[C:82]([OH:84])=O.CN([CH:88]=[O:89])C>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH:68]([C:10]([C:50]1[CH:51]=[CH:46][C:47]([O:89][CH3:88])=[CH:48][CH:49]=1)([C:11](=[O:12])[NH2:13])[N:7]1[C:8](=[O:9])[CH:2]([NH:1][C:82]([C:74]2[NH:73][C:81]3[C:76]([CH:75]=2)=[CH:77][CH:78]=[CH:79][CH:80]=3)=[O:84])[C:3](=[O:35])[N:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:5]2[CH:28]=[CH:27][CH:26]=[CH:25][C:6]1=2)([CH3:67])[CH3:63]

Komponenten

8

Edukt 5

HCID 6228DimethylformamideHCID 72899Indole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 18929586HCID 18929586, Verbindung

Produkt 1

HCID 131720606HCID 131720606, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-(3-Amino-2,4-dioxo-5-pyrdin-2-yl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (276 mg), BOP (244 mg), HOBT (78 mg), DMAP (69 mg) and indole-2-carboxylic acid (98 mg) in DMF (1 ml) was stirred at rt for 18 h. The reaction mixture was diluted with ethyl acetate (15 ml), washed with 1N aqueous sodium hydroxide solution (2×15 ml), water (20 ml), brine (20 ml), dried (K2CO3) and concentrated in vacuo to afford the cude product. Purification by RP-HPLC utilizing a linear gradient (20% A, 80% B to 90% B, 10% C, 30 min) gave the title product (26.6 mg) as a white lyophile;Tr=21.3 min. 1H NMR (300 MHz, CDCl3); 0.98 (2×d, J=7 Hz, 6H), 3.68 (s, 3H), 4.17 (d J=16.6 Hz, 1H), 4.37 (d, J=16.8 Hz, 1H), 4.87 (sept, J=6.8 Hz, 1H), 5.40 (d, J =6.8 Hz, 1H), 6.40 (d, J=5.3 Hz, 1H), 6.75-6.84 (m, 5H), 6.92-6.99 (m, 2H), 7.07 (t, J=7.3 Hz, 1H), 7.09-7.2 (m, 4H), 7.24 (t, J=9.2 Hz, 1H), 7.40 (t, J=9.1 Hz, 2H), 7.52 (d J=7.9 Hz, 1H), 7.72 (m, 2H), 8.38 (d, J=4.4 Hz, 1H), 9.19 (s, 1H). m/z [MH]+ =617.

Aufarbeitung

  1. washwashed with 1N aqueous sodium hydroxide solution (2×15 ml), water (20 ml), brine (20 ml)
  2. dry with materialdried (K2CO3)
  3. concentrationconcentrated in vacuo
  4. customto afford the cude product
  5. customPurification by RP-HPLC
  6. customa linear gradient (20% A, 80% B to 90% B, 10% C, 30 min)

Quellen und Nachweise

ORD-Eintrag
ord-a7cf7e02f8d04b98abc053292cf44d54
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739129

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