1-Aminocyclobutanecarboxylic acid → (E)-3-[2-(1-aminocyclobutyl)-1-methyl-1H-benzoimidazol-5-yl]acrylic acid methyl ester

HRID 731119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 731119
[CH3:1][O:2][C:3](=[O:15])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[C:8]([NH2:14])[CH:7]=1.[NH2:16][C:17]1([C:21](O)=O)[CH2:20][CH2:19][CH2:18]1>C(Cl)Cl.Cl.NC1(C(Cl)=O)CCC1.C(O)(=O)C.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3](=[O:15])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]2[N:12]([CH3:13])[C:21]([C:17]3([NH2:16])[CH2:18][CH2:19][CH2:20]3)=[N:14][C:8]=2[CH:7]=1

Komponenten

7

Edukt 2

HCID 896431-Aminocyclobutanecarboxylic acidHCID 58866234(E)-3-(3-amino-4-methylaminophenyl)acrylic acid methyl ester

Produkt 1

HCID 58866235(E)-3-[2-(1-aminocyclobutyl)-1-methyl-1H-benzoimidazol-5-yl]acrylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittelHCID 21105264Cyclobutanecarbonyl chloride, 1-amino-, hydrochlorideLösungsmittel

Versuchsvorschrift

(E)-3-(3-Amino-4-methylaminophenyl)acrylic acid methyl ester 2-4 from Example 2 (40 mg, 0.194 mmol) was suspended in CH2Cl2 (3 mL) and 1-aminocyclobutanecarboxylic acid chloride hydrochloride, prepared from 1-aminocyclobutanecarboxylic acid following an adaptation of the procedure described by E. S. Uffelman et al. (Org. Lett. 1999, 1, 1157), (31 mg, 0.18 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours and then concentrated to obtain a white solid. The solid was then dissolved in acetic acid (5 mL) and heated to 60° C. for 20 hours. The reaction crude was diluted with aqueous saturated NaHCO3, extracted with CH2Cl2 (2×50 mL) and brine, the organic layer was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure to give (E)-3-[2-(1-aminocyclobutyl)-1-methyl-1H-benzoimidazol-5-yl]acrylic acid methyl ester 3-1 as a light brown foam (53 mg).

Aufarbeitung

  1. additionUffelman et al. (Org. Lett. 1999, 1, 1157), (31 mg, 0.18 mmol) was added
  2. concentrationconcentrated
  3. customto obtain a white solid
  4. temperatureheated to 60° C. for 20 hours
  5. customThe reaction crude
  6. extractionextracted with CH2Cl2 (2×50 mL) and brine
  7. dry with materialthe organic layer was dried over anhydrous MgSO4
  8. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d4d38da37fff46b883681f0cd728f085
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582770B2

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