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Dimethyl Sulfoxide → 1-[5-(1,1-Dimethyl-2-oxo-ethyl)-isoxazol-3-yl]-3-{4-[7-(2-morpholin-4-yl-ethoxy)-benzo[d]imidazo[2,1-b]thiazol-2-yl]-phenyl}-urea

HRID 1038332
ノート
印刷プレビュー

反応式

HRID 1038332 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][C:13]([C:16]1[O:20][N:19]=[C:18]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[N:32]=[C:33]4[N:37]([CH:38]=3)[C:36]3[CH:39]=[CH:40][C:41]([O:43][CH2:44][CH2:45][N:46]5[CH2:51][CH2:50][O:49][CH2:48][CH2:47]5)=[CH:42][C:35]=3[S:34]4)=[CH:27][CH:26]=2)=[O:23])[CH:17]=1)([CH3:15])[CH3:14].C(N(CC)CC)C>ClCCl>[CH3:15][C:13]([C:16]1[O:20][N:19]=[C:18]([NH:21][C:22]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([C:31]3[N:32]=[C:33]4[N:37]([CH:38]=3)[C:36]3[CH:39]=[CH:40][C:41]([O:43][CH2:44][CH2:45][N:46]5[CH2:47][CH2:48][O:49][CH2:50][CH2:51]5)=[CH:42][C:35]=3[S:34]4)=[CH:29][CH:30]=2)=[O:23])[CH:17]=1)([CH3:14])[CH:12]=[O:11]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 461867861-[5-(2-Hydroxy-1,1-dimethyl-ethyl)-isoxazol-3-yl]-3-{4-[7-(2-morpholin-4-yl-ethoxy)-benzo[d]imidazo[2,1-b]thiazol-2-yl]-phenyl}-urea

生成物 1

HCID 462144741-[5-(1,1-Dimethyl-2-oxo-ethyl)-isoxazol-3-yl]-3-{4-[7-(2-morpholin-4-yl-ethoxy)-benzo[d]imidazo[2,1-b]thiazol-2-yl]-phenyl}-urea

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Alternatively, 1-[5-(1,1-dimethyl-2-oxo-ethyl)-isoxazol-3-yl]-3-{4-[7-(2-morpholin-4-yl-ethoxy)-benzo[d]imidazo[2,1-b]thiazol-2-yl]-phenyl}-urea (I-4a) is prepared in the following manner. To a stirred mixture of dimethyl sulfoxide (1 equivalent) in anhydrous dichloromethane at −78° C. under an argon atmosphere is added dropwise oxalyl chloride (0.5 equivalents). After stirring for a further 20 to 40 min, compound 1-[5-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-3-yl]-3-{4-[7-(2-morpholin-4-yl-ethoxy)-benzo[d]imidazo[2,1-b]thiazol-2-yl]-phenyl}-urea (I-1) (0.3 equivalents) is added and the mixture is stirred at −78° C. Triethylamine (1-2 equivalents) is added, and the mixture is allowed to warm to rt, then the mixture is filtered through Celite and concentrated under reduced pressure. The residue is purified by silica gel flash chromatography to afford 1-[5-(1,1-dimethyl-2-oxo-ethyl)-isoxazol-3-yl]-3-{4-[7-(2-morpholin-4-yl-ethoxy)-benzo[d]imidazo[2,1-b]thiazol-2-yl]-phenyl}-urea (I-4a).

後処理

  1. customAlternatively, 1-[5-(1,1-dimethyl-2-oxo-ethyl)-isoxazol-3-yl]-3-{4-[7-(2-morpholin-4-yl-ethoxy)-benzo[d]imidazo[2,1-b]thiazol-2-yl]-phenyl}-urea (I-4a) is prepared in the following manner
  2. stirringthe mixture is stirred at −78° C
  3. filtrationthe mixture is filtered through Celite
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-1f369c10ceee4c628d7acaf761c7a118
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08551963B2

反応ノート

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