Dimethylformamide → 3-[4-(1-carbomethoxy-1-cyclohexyl)methoxyphenyl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

HRID 2399452ノート

反応式

HRID 2399452 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3=[N:14][CH:15]=[CH:16][C:17]([CH3:18])=[C:12]3[N:11]=[C:10]2[CH2:19][CH2:20][CH3:21])=[CH:4][CH:3]=1.[CH2:22]1[O:39][CH2:38]COCCOCCOCCOCCOC1.Br[CH:41]([CH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1)C(OC)=O.CN(C=[O:56])C>>[C:22]([C:46]1([CH2:41][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][N:9]3[C:13]4=[N:14][CH:15]=[CH:16][C:17]([CH3:18])=[C:12]4[N:11]=[C:10]3[CH2:19][CH2:20][CH3:21])=[CH:4][CH:3]=2)[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]1)([O:39][CH3:38])=[O:56]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 2855718-Crown-6HCID 295968Methyl 2-bromo-2-cyclohexylacetateHCID 193856433-(4-hydroxyphenyl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

生成物 1

HCID 193856563-[4-(1-carbomethoxy-1-cyclohexyl)methoxyphenyl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine収率 10%

実験手順

A solution of 0.200 g (0.71 mmol) of 3-(4-hydroxyphenyl)methyl-7-methyl-2-propyl-3H-imidazo [4,5-b]pyridine (Step D, Example 2) dissolved in 0.5 mL of DMF was deprotonated (82 mg KH, 0.188 g 18-crown-6) and alkylated with 0.184 g (0.78 mmol) of commercially available methyl 2-bromo-2-cyclohexylacetate similarly to the procedure described in Example 2, Step E. Purification on a silica gel flash chromatography column eluted with 30% ethyl acetate/hexane afforded 0.029 g (10%) of the title compound.

後処理

  1. customPurification on a silica gel flash chromatography column
  2. washeluted with 30% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-c1d8d46241e5446a99a06ad5ad995741
出典データセット
uspto-grants-1995_09
特許番号
US05449682

反応ノート

読み込み中…