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Tetrahydrofuran → 2-(6-{[Bis-(3-morpholin-4-yl-propyl)-amino]-methyl}-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide

HRID 1667798
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Reaktionsgleichung

Reaktionsgleichung von HRID 1667798
[N:1]1([CH2:7][CH2:8][CH2:9][N:10]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([N+:43]([O-])=O)=[C:25]([NH:27][C:28]3[S:29][C:30]([C:40]([NH2:42])=[O:41])=[C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=4)[N:32]=3)[CH:26]=2)[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O1CCC[CH2:47]1.[Cl-].[NH4+].C(OCC)(OCC)OCC>[Zn].C(O)(=O)C>[N:1]1([CH2:7][CH2:8][CH2:9][N:10]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]3[N:43]=[CH:47][N:27]([C:28]4[S:29][C:30]([C:40]([NH2:42])=[O:41])=[C:31]([C:33]5[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=5)[N:32]=4)[C:25]=3[CH:26]=2)[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1
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Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 31214Ethyl orthoformateHCID 866428572-(5-{[Bis-(3-morpholin-4-yl-propyl)-amino]-methyl}-2-nitro-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide

Produkt 1

HCID 468317702-(6-{[Bis-(3-morpholin-4-yl-propyl)-amino]-methyl}-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a mixture of 0.150 g (0.23 mmole) of 2-(5-{[bis-(3-morpholin-4-yl-propyl)-amino]-methyl}-2-nitro-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (VI.49a), 20 mL of tetrahydrofuran, and 20 mL of saturated ammonium chloride solution was added 0.089 g (1.38 mg-atom) of zinc powder. After 5 minutes the mixture was filtered and the filtrate partitioned between 50 mL of saturated ammonium chloride and 50 mL of tetrahydrofuran. The tetrahydrofuran layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was stirred for 3 hours with 30 mL of acetic acid and 0.178 g (1.2 mmole) of triethyl orthoformate. The mixture was concentrated under reduced pressure, diluted with 100 mL of dichloromethane and washed with saturated sodium bicarbonate solution, then brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-methanol-ammonium hydroxide (92:8:1) to give 0.075 g of 2-(6-{[bis-(3-morpholin-4-yl-propyl)-amino]-methyl}-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (I.49) as a light pink solid. MH+/Z=638.

Aufarbeitung

  1. filtrationAfter 5 minutes the mixture was filtered
  2. customthe filtrate partitioned between 50 mL of saturated ammonium chloride and 50 mL of tetrahydrofuran
  3. dry with materialThe tetrahydrofuran layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. concentrationThe mixture was concentrated under reduced pressure
  7. additiondiluted with 100 mL of dichloromethane
  8. washwashed with saturated sodium bicarbonate solution
  9. dry with materialbrine, dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel chromatography
  12. washeluting with dichloromethane-methanol-ammonium hydroxide (92:8:1)

Quellen und Nachweise

ORD-Eintrag
ord-e5ddf3802b72457e8b25a4e5ea1450d1
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08044213B2

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