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Triethylamine → 7-Chloro-3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1-ethyl-1,2,3,4-tetrahydro-6-nitro-2,4-dioxoquinazoline

HRID 55028
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 55028
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:26])[N:7]([CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]3)[C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[N+:27]([O-:29])=[O:28].Br.[Cl:31][C:32]1[CH:41]=[C:40]2[C:35]([C:36](=[O:51])[N:37]([CH:45]3[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]3)[C:38](=[O:44])[N:39]2[CH2:42][CH3:43])=[CH:34][C:33]=1[N+:52]([O-:54])=[O:53].Cl[C:56]1[C:65]2[C:60](=[CH:61][C:62]([O:68][CH3:69])=[C:63]([O:66][CH3:67])[CH:64]=2)[N:59]=[CH:58][N:57]=1.C(N(CC)CC)C>CO.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:26])[N:7]([CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]3)[C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[N+:27]([O-:29])=[O:28].[Cl:31][C:32]1[CH:41]=[C:40]2[C:35]([C:36](=[O:51])[N:37]([CH:45]3[CH2:50][CH2:49][N:48]([C:56]4[C:65]5[C:60](=[CH:61][C:62]([O:68][CH3:69])=[C:63]([O:66][CH3:67])[CH:64]=5)[N:59]=[CH:58][N:57]=4)[CH2:47][CH2:46]3)[C:38](=[O:44])[N:39]2[CH2:42][CH3:43])=[CH:34][C:33]=1[N+:52]([O-:54])=[O:53]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 229234127-Chloro-3-(1-ethoxycarbonyl-4-piperidinyl)-1-ethyl-1,2,3,4-tetrahydro-6-nitro-2,4-dioxoquinazoline2×HCID 229234787-Chloro-1-ethyl-1,2,3,4-tetrahydro-6-nitro-2,4-dioxo-3-(4-piperidinyl)-quinazoline hydrobromide

Produkt 2

HCID 22923390
7-Chloro-3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1-ethyl-1,2,3,4-tetrahydro-6-nitro-2,4-dioxoquinazoline
HCID 229234127-Chloro-3-(1-ethoxycarbonyl-4-piperidinyl)-1-ethyl-1,2,3,4-tetrahydro-6-nitro-2,4-dioxoquinazoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

The procedure similar to that described in Example 15 was repeated, except that 200.0 mg (0.47 mmol) of 7-chloro-3-(1-ethoxycarbonyl-4-piperidinyl)-1-ethyl-1,2,3,4-tetrahydro-6-nitro-2,4-dioxoquinazoline (Compound t) was used in place of Compound a, whereby 150.6 mg of crude 7-chloro-1-ethyl-1,2,3,4-tetrahydro-6-nitro-2,4-dioxo-3-(4-piperidinyl)-quinazoline hydrobromide was obtained. The product (145.0 mg, 0.31 mmol) was suspended in 10 ml of methanol, and 70 mg (0.31 mmol) of 4-chloro-6,7-dimethoxyquinazoline and 0.11 ml (0.78 mmol) of triethylamine were added thereto, followed by heating under reflux for 1 hour. After the reaction mixture was cooled to room temperature, water was added, and the precipitated crystals were collected by filtration, washed successively with water, methanol, and ether, and dried. Recrystallization of the resulting crude crystals from methanol/water gave 144.6 mg (yield from Compound t: 60%) of Compound 36 as pale yellow crystals.

Aufarbeitung

  1. customwas obtained
  2. temperatureby heating
  3. temperatureunder reflux for 1 hour
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed successively with water, methanol, and ether
  6. customdried
  7. customRecrystallization of the resulting crude crystals from methanol/water
  8. customgave

Quellen und Nachweise

ORD-Eintrag
ord-329c4970ffcc49df9f3a9ebf8e407dcc
Quelldatensatz
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05624926

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