Sodium Iodide → 5-phenyl-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo-[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione hydrochloride

HRID 12753

反応式

HRID 12753 の反応式
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][NH:11][CH2:10]3)=[CH:5][CH:4]=1.[Cl:17][CH2:18][CH2:19][CH2:20][N:21]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24](=[O:33])[NH:23][C:22]1=[O:34].[Na+].[I-].[NH4+].[Cl-]>CN(C=O)C>[ClH:17].[C:27]1([C:25]2[C:24](=[O:33])[NH:23][C:22](=[O:34])[N:21]([CH2:20][CH2:19][CH2:18][N:11]3[CH2:12][C@H:13]4[C@:9]([C:6]5[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][CH:7]=5)([CH2:14]4)[CH2:10]3)[CH:26]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 25517Ammonium ChlorideHCID 589941861-(3-chloropropyl)-5-phenyl-2,4(1H,3H)-pyrimidinedioneHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

生成物 1

HCID 686934935-phenyl-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo-[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione hydrochloride収率 88.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of (1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (Prep4, 40 mg) 1-(3-chloropropyl)-5-phenyl-2,4(1H,3H)-pyrimidinedione (Prep 4, 55 mg), TEA (0.050 mL) and NaI cat. Amount, in DMF (0.5 mL) was heated at 100° C. for 24 hours. Aqueous saturated NH4Cl solution was then added to the mixture and then it was extracted with DCM. The organic phase was dried and concentrated in vacuo. The crude product was purified by a SCX cartridge to give 77 mg of the title compound as free base. HCl (1M in diethyl ether) was added to a solution of the free base in dichloromethane. The mixture was evaporated and the residue triturated with diethyl ether to give the title compound (78 mg).

後処理

  1. extractionit was extracted with DCM
  2. customThe organic phase was dried
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by a SCX cartridge

出典と根拠

ORDレコード
ord-6ec9f3d9adb8408a88df599667c67d5b
出典データセット
uspto-grants-2010_06
特許番号
US07727988B2

関連ノート

読み込み中…