Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 2-[(7-Benzyloxy-isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid methyl ester

HRID 1367891

Reaktionsgleichung

Reaktionsgleichung von HRID 1367891
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:19]([OH:21])=O)[N:15]=[CH:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:46][O:47][C:48]([C:50]1[C:58]2[N:57]=[C:56]([NH2:59])[NH:55][C:54]=2[CH:53]=[CH:52][CH:51]=1)=[O:49]>CN(C=O)C.CCN(C(C)C)C(C)C>[CH3:46][O:47][C:48]([C:50]1[C:58]2[N:57]=[C:56]([NH:59][C:19]([C:14]3[N:15]=[CH:16][C:17]4[C:12]([CH:13]=3)=[CH:11][CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:18]=4)=[O:21])[NH:55][C:54]=2[CH:53]=[CH:52][CH:51]=1)=[O:49]

Komponenten

6

Edukt 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24730367methyl 2-amino-1H-benzo[d]imidazole-4-carboxylate2×HCID 669402157-Benzyloxy-isoquinoline-3-carboxylic acid

Produkt 1

HCID 587244182-[(7-Benzyloxy-isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid methyl esterAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

0.70 g (2.5 mmol) of 7-benzyloxy-isoquinoline-3-carboxylic acid synthesized above, 1.0 g (2.7 mmol) of HBTU in a mixture of 7.5 ml of DMF and 1.7 mL of DIEA was reacted with 0.48 g (2.5 mmol) of 2-Amino-3H-benzoimidazole-4-carboxylic acid methyl ester (Intermediate A) as described in general procedure A. 2-[(7-Benzyloxy-isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid methyl ester (1.0 g, 88%) was isolated after column chromatography using 1:1 ethyl acetate and hexane as an eluents. LCMS: 453 (M+1)+.

Quellen und Nachweise

ORD-Eintrag
ord-94856ad769a34fd08d5d5c79359063e5
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893267B2

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