Triethylamine → N,N-dimethyl-N~2~-({[4'-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]amino}carbonyl)glycinamide

HRID 1715286

Reaktionsgleichung

Reaktionsgleichung von HRID 1715286
[CH3:1][C:2]1[N:3]=[C:4]([NH:20][C:21](N2C=CN=C2)=[O:22])[S:5][C:6]=1[C:7]1[N:8]=[C:9]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])[S:10][CH:11]=1.C(O)(=O)C.[CH3:32][N:33]([CH3:38])[C:34](=[O:37])[CH2:35][NH2:36].C(N(CC)CC)C>CN(C=O)C>[CH3:32][N:33]([CH3:38])[C:34](=[O:37])[CH2:35][NH:36][C:21]([NH:20][C:4]1[S:5][C:6]([C:7]2[N:8]=[C:9]([C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[O:13])[S:10][CH:11]=2)=[C:2]([CH3:1])[N:3]=1)=[O:22]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 533990092-Amino-N,N-dimethylacetamide acetateHCID 59465567N-[4'-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]-1H-imidazole-1-carboxamide

Produkt 1

HCID 11990108N,N-dimethyl-N~2~-({[4'-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]amino}carbonyl)glycinamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To N-[4′-methyl-2-(morpholin-4-ylcarbonyl)-4,5′-bi-1,3-thiazol-2′-yl]-1H-imidazole-1-carboxamide, prepared as in Step 3 of Example 36, described above (75 mg; 0.19 mmol; 1 eq.) is added DMF (3 ml), glycine dimethylamide acetate (Chem-Impex) (30.1 mg; 0.19 mmol; 1 eq.) and triethylamine (57 μl; 0.41 mmol; 2.20 eq.). The mixture is stirred 3 hours at rt. Solvents are evaporated and the crude product is crystallized in MeOH, affording Compound (46) as a light yellow solid (49 mg; 60%). 1H NMR (DMSO-d6, 300 MHz) δ 2.44 (s, 3H), 2.86 (s, 3H), 2.94 (s, 3H), 3.68 (m, 6H), 4.01 (m, 2H), 4.33 (m, 2H), 6.83 (m, 1H), 7.91 (s, 1H), 10.70 (br s, 1H). M− (ESI): 437.15; M+ (ESI): 439.09. HPLC (method A), Rt: 2.30 min (purity: 99%).

Aufarbeitung

  1. customSolvents are evaporated
  2. customthe crude product is crystallized in MeOH

Quellen und Nachweise

ORD-Eintrag
ord-677a61ddda72456e955578dca060b746
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799814B2

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