4-Methyl-2-Pentanol → 4-[(2-cyclopentyl-4,4-diethyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-N-(2,2-dimethyl-3-pyrrolidin-1-yl-propyl)-3-methoxy-benzamide

HRID 2234318

Reaktionsgleichung

Reaktionsgleichung von HRID 2234318
Cl[C:2]1[N:12]=[C:11]2[C:5]([N:6]([CH3:23])[C:7](=[O:22])[C:8]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:9][N:10]2[CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:36][C:37]1[CH:55]=[CH:54][C:40]([C:41]([NH:43][CH2:44][C:45]([CH3:53])([CH3:52])[CH2:46][N:47]2[CH2:51][CH2:50][CH2:49][CH2:48]2)=[O:42])=[CH:39][C:38]=1[O:56][CH3:57].CC(C)CC(O)C>CO>[CH:13]1([N:10]2[CH2:9][C:8]([CH2:20][CH3:21])([CH2:18][CH3:19])[C:7](=[O:22])[N:6]([CH3:23])[C:5]3[C:11]2=[N:12][C:2]([NH:36][C:37]2[CH:55]=[CH:54][C:40]([C:41]([NH:43][CH2:44][C:45]([CH3:52])([CH3:53])[CH2:46][N:47]4[CH2:51][CH2:50][CH2:49][CH2:48]4)=[O:42])=[CH:39][C:38]=2[O:56][CH3:57])=[N:3][CH:4]=3)[CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

6

Edukt 4

HCID 79104-Methyl-2-PentanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 686858814-amino-N-(2,2-dimethyl-3-pyrrolidin-1-yl-propyl)-3-methoxy-benzamide2×HCID 8661756310-Chloro-2-cyclopentyl-4,4-diethyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one2×

Produkt 1

HCID 686849234-[(2-cyclopentyl-4,4-diethyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-N-(2,2-dimethyl-3-pyrrolidin-1-yl-propyl)-3-methoxy-benzamideAusbeute 27,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

10-chloro-2-cyclopentyl-4,4-diethyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one (Intermediate 250; 111 mg, 0.33 mmol), p-toluenesulphonic acid monohydrate (155 mg, 0.81 mmol) and 4-amino-N-(2,2-dimethyl-3-pyrrolidin-1-yl-propyl)-3-methoxy-benzamide (Intermediate 206; 100 mg, 0.33 mmol) were added to 4-methyl-2-pentanol (7 mL). The reaction was heated at 120° C. over the weekend. The sample was transferred to an SCX cartridge (10 g) pre-wet with methanol, then washed with methanol and eluted with methanolic ammonia. Product containing fractions were combined and evaporated and the resultant material purified by base modified reverse phase preparative HPLC to yield the title compound as a white solid (55 mg, 27%).

Aufarbeitung

  1. washwashed with methanol
  2. washeluted with methanolic ammonia
  3. additionProduct containing fractions
  4. customevaporated
  5. customthe resultant material purified by base modified reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-60b4843b9356418ca573b23f27335ab6
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709471B2

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