Isopropanol → 2-[5-Chloro-4-(2-methoxy-4-morpholin-4-yl-phenylamino)-pyrimidin-2-ylamino]-5,6,8,9-tetrahydro-benzocyclohepten-7-one

HRID 1040695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040695
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19]N[CH2:17][CH2:16]3)=[CH:11][C:10]=2[O:21][CH3:22])[C:5]([Cl:23])=[CH:4][N:3]=1.[NH2:24][C:25]1[CH:26]=[CH:27][C:28]2[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30][C:29]=2[CH:36]=1.C([OH:40])(C)C>Cl.O1CCOCC1.O>[Cl:23][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:16][CH2:17][O:40][CH2:19][CH2:20]3)=[CH:11][C:10]=2[O:21][CH3:22])=[N:7][C:2]([NH:24][C:25]2[CH:26]=[CH:27][C:28]3[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30][C:29]=3[CH:36]=2)=[N:3][CH:4]=1

Komponenten

6

Edukt 3

HCID 3776IsopropanolHCID 450982242-Amino-8,9-dihydro-5H-benzo[7]annulen-7(6H)-oneHCID 86633856(2,5-Dichloro-pyrimidin-4-yl)-(2-methoxy-4-piperazin-1-yl-phenyl)-amine

Produkt 1

HCID 668294972-[5-Chloro-4-(2-methoxy-4-morpholin-4-yl-phenylamino)-pyrimidin-2-ylamino]-5,6,8,9-tetrahydro-benzocyclohepten-7-oneAusbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

Into a microwave vial was added (2,5-dichloro-pyrimidin-4-yl)-(2-methoxy-4-piperazin-1-yl-phenyl)-amine (60 mg, 0.0002 mol) and 2-amino-5,6,8,9-tetrahydro-benzocyclohepten-7-one (38 mg, 0.00022 mol) in isopropyl alcohol (5 mL, 0.06 mol) with 3-4 drops of 4M HCl in dioxane-water. The mixture was subjected to microwaves at 130° C. for 10 minutes. Trace starting materials were present so the reaction mixture was resubjected to the same conditions. The resulting solid was collected by filtration and washed with cold methylene chloride and dried in a vacuum oven at 50° C. overnight to give 50 mg of 2-[5-chloro-4-(2-methoxy-4-morpholin-4-yl-phenylamino)-pyrimidin-2-ylamino]-5,6,8,9-tetrahydro-benzocyclohepten-7-one as an off-white solid. MP: 212-215° C.; 1HNMR (400 MHz, DMSO-d6) δ 9.19 (s, 1H), 8.11 (s, 1H), 8.04 (s, 1H), 7.54 (s, 1H), 7.50 (d, 1H, J=8 Hz), 7.25 (d, 1H, J=9, 17 Hz), 6.99 (d, 1H, J=8 Hz), 6.68 (d, 1H, J=9 Hz), 6.51 (d, 1H, J=9 Hz), 3.77 (s, 7H), 3.15 (m, 4H), 2.75 (m, 2H), 2.60 (m, 2H), 2.47 (m, 4H); MS (m/e) 494 (M+1).

Aufarbeitung

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with cold methylene chloride
  3. customdried in a vacuum oven at 50° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-d1f6446b46a24592a4ed807eb6bfa542
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

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