Diisopropylethylamine → 4-{3-[5-(2-Methoxy-1,1-dimethyl-ethyl)-indan-1-yl]-ureido}-indazole-1-carboxylic acid methyl ester

HRID 2223404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223404
[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[C:9]([NH:14][C:15]([O:17]N3C(=O)CCC3=O)=O)[CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6]1)=[O:4].[CH3:25][O:26][CH2:27][C:28]([C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[CH:36]([NH2:40])[CH2:35][CH2:34]2)([CH3:30])[CH3:29].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[C:9]([NH:14][C:15]([NH:40][CH:36]3[C:37]4[C:33](=[CH:32][C:31]([C:28]([CH3:30])([CH3:29])[CH2:27][O:26][CH3:25])=[CH:39][CH:38]=4)[CH2:34][CH2:35]3)=[O:17])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6]1)=[O:4]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 11313556methyl 4-({[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}amino)-1H-indazole-1-carboxylateHCID 671874325-(2-Methoxy-1,1-dimethyl-ethyl)-indan-1-ylamine

Produkt 1

HCID 671881034-{3-[5-(2-Methoxy-1,1-dimethyl-ethyl)-indan-1-yl]-ureido}-indazole-1-carboxylic acid methyl esterAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(2,5-dioxo-pyrrolidin-1-yloxycarbonylamino)-indazole-1-carboxylic acid methyl ester (0.66 g, 2.00 mmol) was added to a solution of 5-(2-methoxy-1,1-dimethyl-ethyl)-indan-1-ylamine (0.46 g, 2.1 mmol) and diisopropylethylamine (0.26 g, 2.00 mmol) in DMF (6 mL) under nitrogen atmosphere at ambient temperature. After 30 minutes the mixture was diluted with water (6 mL). The resulting precipitate was filtered off, washed with aqueous MeCN twice and dried to obtain desired product (0.48 g, 55%). NMR (DMSO-d6): 8.82 (s, 1H), 8.40 (s, 1H), 7.95 (s, 1H), 7.88 (d, J 7.5 Hz, 1H), 7.69 (d, J 8 Hz, 1H), 7.52 (t, J 8 Hz, 1H), 7.24 (m, 2H), 6.70 (d, J 7.5 Hz, 1H), 5.18 (m, 1H), 4.02 (m, 3H), 3.38 (s, 2H), 3.20 (s, 3H), 3.10-2.72 (m, 2H), 2.42 (m, 1H), 1.83 (m, 1H), 1.14 (s, 6H). MS (DCI): 437 (M+1).

Aufarbeitung

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with aqueous MeCN twice
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3d4d63eb5d8d45eca156828e93fffe36
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375126B2

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