Methanol → 1-benzyl-2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid

HRID 1367856

Reaktionsgleichung

C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH:14][C:15]([C:17]3[N:18]=[CH:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:16])[N:10]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].CO.[Li+].[OH-]>C1COCC1>[CH2:27]([N:10]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=2[N:12]=[C:11]1[NH:14][C:15]([C:17]1[N:18]=[CH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:16])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

To a solution of 45 mg (0.12 mmol) of (1-benzyl-2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid methyl ester (Example 134) in THF (1 mL) was added methanol (1 mL) and 1 N LiOH solution (1 mL). The reaction was heated at 65° C. for 45 min., and the conversion was monitored by TLC. After cooling to room temperature, the organic solvents were removed under reduced pressure, the reaction residue was acidified (pH=2) by addition of 1 N HCl solution. The solid product was collected by filtration and further dried to afford 43 mg (100%) 1-benzyl-2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid. LCMS: 423 (M+1)+.

Aufarbeitung

temperatureAfter cooling to room temperature
customthe organic solvents were removed under reduced pressure
additionby addition of 1 N HCl solution
filtrationThe solid product was collected by filtration
customfurther dried

Quellen und Nachweise

ORD-Eintrag: ord-b2ae72c4f3a34f39b80fd9e34088cba5
Quelldatensatz: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07893267B2

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