Diisopropylethylamine → HCID 178490377、化合物

HRID 333411ノート

反応式

HRID 333411 の反応式
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH:8][C:9](=[O:24])[NH:10][CH:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:12]([OH:14])=O)[N:3]=[CH:2]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[C:57]([C:59]1([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1)#[N:58]>ClCCl.CN(C)C=O>[C:57]([C:59]1([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[CH2:60][CH2:61][N:62]([C:12](=[O:14])[CH:11]([NH:10][C:9]([NH:8][CH2:7][CH2:6][C:4]2[N:3]=[CH:2][NH:1][CH:5]=2)=[O:24])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:63][CH2:64]1)#[N:58]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 30849734-Phenylpiperidine-4-carbonitrile hydrochlorideHCID 178490381HCID 178490381、化合物

生成物 1

HCID 178490377HCID 178490377、化合物収率 17%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To 300 mg (0.90 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxy-phenyl)propanoic acid dissolved in 3.5 mL of dichloromethane and 1.5 mL of dimethylformamide are added 0.46 mL (2.7 mmol) of diisopropylethylamine, 318 mg (0.99 mmol) of TBTU and 220 mg (0.99 mmol) of 4-cyano-4-phenylpiperidine hydrochloride. After 16 hours, the solution is washed with saturated sodium hydrogen carbonate solution and the organic products are extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and concentrated. The crude product obtained is purified by filtration on a pad of silica (eluent: 7/3 dichloromethane/methanol). 75 mg of 1-[2-(4-cyano-4-phenylpiperidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]-3-[2-(1H-imidazol-4-yl)ethyl]urea in the form of a white powder are obtained in a yield of 17%.

後処理

  1. washthe solution is washed with saturated sodium hydrogen carbonate solution
  2. extractionthe organic products are extracted with dichloromethane
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product obtained
  7. filtrationis purified by filtration on a pad of silica (eluent: 7/3 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-828d5a7d6b8443ea96684b9e139dcc0b
出典データセット
uspto-grants-2014_11
特許番号
US08877968B2

反応ノート

読み込み中…