Acetamidine monohydrochloride → 13-Chloro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,12-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene

HRID 1530713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530713
[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11](I)=[CH:10]3)=[CH:4][N:3]=1.Cl.[C:18]([NH2:21])(=[NH:20])[CH3:19].[CH3:22][C:23]1([CH3:63])C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Cl.[CH:65]([NH:68]N)(C)C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C(O)(=O)C>[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11]([C:65]2[N:68]([CH:23]([CH3:63])[CH3:22])[N:21]=[C:18]([CH3:19])[N:20]=2)=[CH:10]3)=[CH:4][N:3]=1

Komponenten

8

Edukt 4

HCID 67170Acetamidine monohydrochlorideHCID 855731-Isopropylhydrazine hydrochlorideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 5820436210-Chloro-2-iodo-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine

Produkt 1

HCID 8667148313-Chloro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,12-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaeneAusbeute 373,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 13-chloro-4-iodo-9-oxa-3,6,12-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (3.00 g, 8.63 mmol), acetamidine hydrochloride (984 mg, 10.4 mmol), Pd(OAc)2 (194 mg, 0.870 mmol), and Xantphos (998 mg, 1.73 mmol) in DMF (20.0 mL) and TEA (5.0 mL) was heated at 40° C. under CO (1 atm) for 3 hrs. After cooling down, isopropylhydrazine hydrochloride (1.05 g, 9.50 mmol) and acetic acid (20.0 mL) were added. The resulting mixture was heated to 65° C. and stirred at this temperature for 1 hr. At the end of reaction, solvents were removed and the residue was poured into water (2000 mL). The solid was collected and washed with acetone to give the desired product (2.23 g, 73% yield) as a yellow solid. LCMS m/z [M+H]+ 345.2.

Aufarbeitung

  1. temperatureAfter cooling down
  2. temperatureThe resulting mixture was heated to 65° C.
  3. customAt the end of reaction, solvents
  4. customwere removed
  5. additionthe residue was poured into water (2000 mL)
  6. customThe solid was collected
  7. washwashed with acetone

Quellen und Nachweise

ORD-Eintrag
ord-761abcbf4a364caa8b40364379ffc363
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090628B2

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