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

HRID 2111981노트

반응식

HRID 2111981 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-ce62e8e45eb648f38669fee6c0fc2c9f
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521461B2

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