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Sodium borohydride → N-(4-{4-amino-7-[5-(hydroxymethyl)-2-furyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

HRID 17204
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17204
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:32]2[O:33][C:34]([CH:37]=[O:38])=[CH:35][CH:36]=2)=[CH:4][N:3]=1.[BH4-].[Na+]>CN(C)C=O.CO>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:32]2[O:33][C:34]([CH2:37][OH:38])=[CH:35][CH:36]=2)=[CH:4][N:3]=1
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Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 18451275N-{4-[4-amino-7-(5-formyl-2-furyl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1H-indole-2-carboxamide

Produkt 1

HCID 18451278N-(4-{4-amino-7-[5-(hydroxymethyl)-2-furyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamideAusbeute 3,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A mixture of N-{4-[4-amino-7-(5-formyl-2-furyl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1H-indole-2-carboxamide (0.060 g, 0.12 mmol) and sodium borohydride (0.013 g, 0.344 mmol) in N,N-dimethylformamide (4 mL) and methanol (4 mL) was stirred at ambient temperature for 18 hours. The solvent was removed in vacuo and the residue was partitioned between dichloromethane (10 mL) and 0.1 N hydrochloric acid (10 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (3×10 mL). The combined organic layers were dried over anhydrous magnesium sulfate and the solvent was removed in vacuo. The residue was purified by preparative RP-HPLC (Rainin C18, 8 mm, 300 Å, 25 cm; 40% acetonitrile—0.1M ammonium acetate isocratic for 5 minutes, then 40-100% acetonitrile—0M ammonium acetate over 30 min, 21 ml/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyophilized to give the title compound (2.1 mg, 0.004 mmol) as a white solid.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between dichloromethane (10 mL) and 0.1 N hydrochloric acid (10 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (3×10 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by preparative RP-HPLC (Rainin C18, 8 mm, 300 Å, 25 cm
  8. wait40% acetonitrile—0.1M ammonium acetate isocratic for 5 minutes
  9. wait40-100% acetonitrile—0M ammonium acetate over 30 min
  10. customThe acetonitrile was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0f232c353f034161a44811877ec19092
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737160B2

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