Diisopropylethylamine → Methyl 2-[(4-{2-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}carbonyl)amino]ethyl}phenoxy)methyl]benzoate

HRID 2111981ノート

反応式

HRID 2111981 の反応式
[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[S:5][C:6]=1[C:7]([OH:9])=O.Cl.[NH2:21][CH2:22][CH2:23][C:24]1[CH:41]=[CH:40][C:27]([O:28][CH2:29][C:30]2[CH:39]=[CH:38][CH:37]=[CH:36][C:31]=2[C:32]([O:34][CH3:35])=[O:33])=[CH:26][CH:25]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[S:5][C:6]=1[C:7]([NH:21][CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:28][CH2:29][C:30]2[CH:39]=[CH:38][CH:37]=[CH:36][C:31]=2[C:32]([O:34][CH3:35])=[O:33])=[CH:40][CH:41]=1)=[O:9]

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27756634-Methyl-2-(4-(trifluoromethyl)phenyl)-5-thiazolecarboxylic acidHCID 68872919Methyl 2-{[4-(2-aminoethyl)phenoxy]methyl}benzoate hydrochloride

生成物 1

HCID 68869761Methyl 2-[(4-{2-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}carbonyl)amino]ethyl}phenoxy)methyl]benzoate収率 61.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylic acid (50 mg, 0.174 mmol) and methyl 2-{[4-(2-aminoethyl)phenoxy]methyl}benzoate hydrochloride (59 mg, 0.183 mmol) were mixed in DMF (4 ml) and the mixture was then cooled in an ice-bath. TBTU (59 mg, 0.183 mmol) was added and followed by DIPEA (47.2 mg, 0.366 mmol). The mixture was stirred at room temperature overnight. Ethyl acetate and sodium hydrogencarbonate aqueous solution (sat.) were added. The two phases were separated. The organic phase was washed with water and dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM and then MeOH/DCM (0.5:99.5) as eluant gave 59 mg the desired product, white solid, yield 61%.

後処理

  1. temperaturethe mixture was then cooled in an ice-bath
  2. customThe two phases were separated
  3. washThe organic phase was washed with water
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated

出典と根拠

ORDレコード
ord-ce62e8e45eb648f38669fee6c0fc2c9f
出典データセット
uspto-grants-2009_04
特許番号
US07521461B2

反応ノート

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