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

반응식

HRID 12753 반응식
[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

참가 물질

6

반응물 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

생성물 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 hydrochloride수율 88.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6ec9f3d9adb8408a88df599667c67d5b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727988B2

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