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1-Hydroxybenzotriazole → N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]isoquinoline-3-carboxamide

HRID 353888
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Reaktionsgleichung

Reaktionsgleichung von HRID 353888
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=O)[N:2]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH2:36][CH2:37][CH2:38][CH2:39][N:40]1[C:52]2[C:51]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[N:45]=[C:44]([NH2:53])[C:43]=2[N:42]=[C:41]1[CH2:54][CH2:55][CH2:56][CH3:57]>CN1CCCC1=O>[NH2:53][C:44]1[C:43]2[N:42]=[C:41]([CH2:54][CH2:55][CH2:56][CH3:57])[N:40]([CH2:39][CH2:38][CH2:37][NH:36][C:11]([C:3]3[N:2]=[CH:1][C:10]4[C:5]([CH:4]=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)=[O:13])[C:52]=2[C:51]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[N:45]=1
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Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 124656Isoquinoline-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 223444131-(3-aminopropyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Produkt 1

HCID 23512702N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]isoquinoline-3-carboxamide
Ausbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Versuchsvorschrift

Isoquinoline-3-carboxylic acid (1.05 g, 6.05 mmol) was stirred in 1-methyl-2-pyrrolidinone (50 mL). 1-Hydroxybenzotriazole (885 mg, 6.55 mmol) was added in a single portion. This solution was stirred for 15-20 minutes and then cooled in an ice bath. 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.26 g, 6.55 mmol) was added in small portions over a period of 10 minutes. The solution was stirred for 1 hour and then added dropwise to a solution of 1-(3-aminopropyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (1.50 g, 5.04 mmol) in 1-methyl-2-pyrrolidinone (100 mL). After 3 hours the reaction mixture was poured into distilled water (800 mL). A solid precipitated. This material was stirred for 5 hours, isolated by filtration and then air dried over the weekend. The solid was taken up in chloroform (100 mL) and then purified by column chromatography (silica gel eluting sequentially with chloroform (1 L), 1% methanol in chloroform (1 L) and 5% methanol in chloroform (1 L)). The purified material was slurried with hot acetonitrile, cooled, isolated by filtration and then dried in a vacuum oven to provide 1.72 g of N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]isoquinoline-3-carboxamide as a solid, m.p. 203.8-205.3° C. Analysis: Calculated for C27H28N6O: % C, 71.66; % H, 6.24; % N, 18.57. Found: % C, 71.63; % H, 6.17; % N, 18.57.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. stirringThe solution was stirred for 1 hour
  3. additionAfter 3 hours the reaction mixture was poured
  4. distillationinto distilled water (800 mL)
  5. customA solid precipitated
  6. stirringThis material was stirred for 5 hours
  7. customisolated by filtration
  8. customair dried over the weekend
  9. custompurified by column chromatography (silica gel eluting sequentially with chloroform (1 L), 1% methanol in chloroform (1 L) and 5% methanol in chloroform (1 L))
  10. temperaturecooled
  11. customisolated by filtration
  12. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-e4e83d01c59645e0957b5ae87b9655bf
Quelldatensatz
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06756382B2

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