Hydrochloric Acid → 1-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-cyclopropanecarboxylic acid

HRID 1480945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1480945
CO[C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:25][CH2:26][C:27]1([C:30]([OH:32])=[O:31])[CH2:29][CH2:28]1.C[O-].[Na+].Cl>CO.O>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:25][CH2:26][C:27]2([C:30]([OH:32])=[O:31])[CH2:29][CH2:28]2)=[O:4])[N:6]=1)#[N:24]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 150339011-(Aminomethyl)cyclopropanecarboxylic acidHCID 89812860HCID 89812860, Verbindung

Produkt 1

HCID 898130731-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-cyclopropanecarboxylic acidAusbeute 25,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

After a mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (101 mg, 0.318 mmol), 1-aminomethyl-cyclopropanecarboxylic acid (110 mg, 0.955 mmol, prepared according to literature: Ohno, Mitsuru et al Synlett 1991, 919-920), and NaOMe in MeOH (1.6 mL, 0.5 M solution) was microwaved at 120° C. for 1 h, the reaction mixture was cooled, diluted with water and acidified with 2 M HCl aqueous solution, the resulted solids were collected via filtration, water-washed and air-dried to give solids, which were further column purified to give the desired product (33 mg). LC MS ESI+: 404 (M+1)+.

Aufarbeitung

  1. customwas microwaved at 120° C. for 1 h
  2. temperaturethe reaction mixture was cooled
  3. filtrationthe resulted solids were collected via filtration, water-
  4. washwashed
  5. customair-dried
  6. customto give solids, which
  7. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-bd7f705b2cf4488db5ac93c66b5788fa
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409892B2

Notizen zur Reaktion

Wird geladen…