Toluene → 4-[(5S*,9R*)-7-Benzyl-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-9-yl]-benzonitrile

HRID 456720

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HRID 456720 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])/[C:12](=[CH:15]\[C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)/[N:11]([CH3:24])[C:10]2=[O:25])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:26]1N2CN3CN(C2)[CH2:28][N:27]1[CH2:34]3.C(NCC(O)=O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C1(C)C=CC=CC=1>CN1CCCC1=O>[CH2:26]([N:27]1[CH2:34][C@@H:15]([C:16]2[CH:17]=[CH:18][C:19]([C:20]#[N:21])=[CH:22][CH:23]=2)[C@:12]2([N:11]([CH3:24])[C:10](=[O:25])[N:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)[C:13]2=[O:14])[CH2:28]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 4101HexamethylenetetramineHCID 869652-(Benzylamino)acetic acidHCID 10270593(E)-4-((1-(3,5-Dichlorophenyl)-3-methyl-2,5-dioxoimidazolidin-4-ylidene)methyl)benzonitrile2회

생성물 1

HCID 119945114-[(5S*,9R*)-7-Benzyl-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-9-yl]-benzonitrile

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
140 °C

실험 절차

A mixture of (E)-4-((1-(3,5-dichlorophenyl)-3-methyl-2,5-dioxoimidazolidin-4-ylidene)methyl)benzonitrile (1.05 g, 2.82 mmol), hexamethylenetetramine (0.395 g, 2.82 mmol), N-benzylglycine (1.17 g, 7.05 mmol), toluene (5 ml), and 1-methyl-2-pyrrolidinone (NMP, 10 ml) was heated to 140° C. The extent of reaction was monitored by HPLC. After 72 hours, the reaction had stopped short of completion. The ratio of product to starting material ((E)-4-((1-(3,5-dichlorophenyl)-3-methyl-2,5-dioxoimidazolidin-4-ylidene)methyl)benzonitrile) was 1.36:1. Mass spectra of the mixture indicated the presence of the desired product. The mixture was washed with water and extracted into toluene. The impure product was obtained as an oil. Comparison of the product obtained to authentic material was made by HPLC. The ratio of the desired (5S, 9R) isomer to the undesired was 19:1.

후처리

  1. customThe extent of reaction

출처 및 근거

ORD 기록
ord-2d6bc040ace94bfc83405eb1ce3346cd
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186727B2

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