2486-69-3 → 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid

HRID 220723

Reaktionsgleichung

Reaktionsgleichung von HRID 220723
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH3:21])[C:7](=[O:20])[C:8]([F:19])([F:18])[CH2:9][N:10]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:11]=2[N:12]=1.[NH2:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][C:24]=1[O:32][CH3:33]>Cl.CC(O)C>[CH:13]1([N:10]2[CH2:9][C:8]([F:19])([F:18])[C:7](=[O:20])[N:6]([CH3:21])[C:5]3[CH:4]=[N:3][C:2]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][C:24]=4[O:32][CH3:33])=[N:12][C:11]2=3)[CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

5

Edukt 2

HCID 2880572486-69-3HCID 579555742-Chloro-9-cyclopentyl-7,7-difluoro-5-methyl-8,9-dihydro-5H-pyrimido[4,5-B][1,4]diazepin-6(7H)-one

Produkt 1

HCID 252529054-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

2-Chloro-9-cyclopentyl-7,7-difluoro-5-methyl-8,9-dihydro-5H-pyrimido[5,4-b][1,4]diazepin-6(7H)-one (obtained above), 4-amino-3-methoxy benzoic acid (334 mg, 2 mmol), i-PrOH (10 mL) and conc. HCl (10 drops) were heated to 100° C. overnight. The reaction mixture was then cooled to room temperature, concentrated and redissolved in MeOH, treated with NaOH and refluxed for 1 hr. After which, it was concentrated, acidified with HCl and filtered to give the title as a tan solid (300 mg). [M+H] calc'd for C21H23F2N5O4, 448; found 448.

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionredissolved in MeOH
  3. additiontreated with NaOH
  4. temperaturerefluxed for 1 hr
  5. concentrationAfter which, it was concentrated
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-8936ff2a70b34497bcb94b245797cc00
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202990B2

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