Diisopropylethylamine → 1-(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)-3-(3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)phenyl)urea

HRID 1917977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1917977
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:19])OC2C=CC=CC=2)[N:7]([CH3:20])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:32]=1[O:33][CH2:34][CH2:35][O:36][CH3:37])[N:29]=[CH:28][N:27]=[C:26]2[O:38][C:39]1[CH:40]=[C:41]([CH:43]=[CH:44][CH:45]=1)[NH2:42].C(N(C(C)C)CC)(C)C>CN(C1C=CN=CC=1)C>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:42][C:41]2[CH:43]=[CH:44][CH:45]=[C:39]([O:38][C:26]3[C:25]4[C:30](=[CH:31][C:32]([O:33][CH2:34][CH2:35][O:36][CH3:37])=[C:23]([O:22][CH3:21])[CH:24]=4)[N:29]=[CH:28][N:27]=3)[CH:40]=2)=[O:19])[N:7]([CH3:20])[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 46196890phenyl 3-tert-butyl-1-methyl-1H-pyrazol-5-ylcarbamateHCID 668758053-(6-Methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)aniline

Produkt 1

HCID 442429291-(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)-3-(3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)phenyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

The procedure in 138B was used to react the carbamate from Example 157A (123 mg, 0.45 mmol) with 3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)aniline from Example 117B (103 mg, 0.30 mmol). To this solution was added diisopropylethyl amine (78 μL, 0.45 mmol) and DMAP (3.6 mg, 0.03 mmol). The reaction was concentrated to dryness. The resulting oil purified by silica gel chromatography eluting with ethyl acetate/dichloromethane 10-50% over 60 minutes. The main peak concentrated to a solid weighing 126 mg. 1H (DMSO-d6) 9.10 (s, 1H), 8.70 (s, 2H), 7.65 (m, 2H), 7.50 (m, 2H), 7.30 (m, 1H), 7.15 (s, 1H), 6.95 (m, 1H), 6.00 (s, 1H), 4.40 (s, 2H), 4.00 (s, 3H), 3.85 (s, 2H), 3.60 (s, 3H), 3.40 (s, 3H), 1.25 (s, 9H). LCMS (ESI) m/z 521 (M+H)

Aufarbeitung

  1. concentrationThe reaction was concentrated to dryness
  2. customThe resulting oil purified by silica gel chromatography
  3. washeluting with ethyl acetate/dichloromethane 10-50% over 60 minutes
  4. concentrationThe main peak concentrated to a solid

Quellen und Nachweise

ORD-Eintrag
ord-bd107727142b4246aba9d0245e248fa6
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618289B2

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