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

HRID 1687005ノート

反応式

HRID 1687005 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-b1e2eacb24774cfeb6bf597ff40dfe6f
出典データセット
uspto-grants-2012_04
特許番号
US08148391B2

反応ノート

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