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

HRID 1687005노트

반응식

HRID 1687005 반응식
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

참가 물질

6

반응물 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

생성물 1

HCID 668294972-[5-Chloro-4-(2-methoxy-4-morpholin-4-yl-phenylamino)-pyrimidin-2-ylamino]-5,6,8,9-tetrahydro-benzocyclohepten-7-one수율 50.6%

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-b1e2eacb24774cfeb6bf597ff40dfe6f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148391B2

반응 노트

불러오는 중…