HCID 23511825, 화합물 → methyl 4-[N-[1-[3-methoxy-4-[N'-(2-fluorophenyl)ureido]phenylacetyl]-2-pyrrolidinyl methyl]-N-methylamino]-3-nitrobenzoate

HRID 350397노트

반응식

HRID 350397 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])=[O:11].[N+:24]([C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][C:36]=1[N:37]([CH2:39][CH:40]1[CH2:44][CH2:43][CH2:42][NH:41]1)[CH3:38])[C:30]([O:32][CH3:33])=[O:31])([O-:26])=[O:25]>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOCC.C1C=CC2N(O)N=NC=2C=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:41]2[CH2:42][CH2:43][CH2:44][CH:40]2[CH2:39][N:37]([C:36]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][C:27]=2[N+:24]([O-:26])=[O:25])[CH3:38])=[O:23])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])=[O:11]

참가 물질

7

반응물 2

HCID 23511825HCID 23511825, 화합물HCID 23511932methyl 3-nitro-4-[N-(2-pyrrolidinyl)methyl-N-methylamino]benzoate

생성물 1

HCID 69332166methyl 4-[N-[1-[3-methoxy-4-[N'-(2-fluorophenyl)ureido]phenylacetyl]-2-pyrrolidinyl methyl]-N-methylamino]-3-nitrobenzoate수율 105.5%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 757711-Hydroxybenzotriazole촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-methoxy-4-[N′-(2-fluorophenyl)ureido]phenylacetic acid (630.0 mg, 1.979 mmol), methyl 3-nitro-4-[N-(2-pyrrolidinyl)methyl-N-methylamino]benzoate (553.0 mg, 1.885 mmol), EDC(Hydrochloride) (542.0 mg, 2.827 mmol), HOBt (25.5 mg, 0.189 mmol), and DMAP (23.1 mg, 0.189 mmol) in DMF (5.0 mL) was stirred at room temp. for 2 hr. The mixture was diluted with Et2O, washed with brine, and dried over Na2SO4. The solvent was removed under a reduced pressure, and the residue was chromatographed on silica-gel with CHCl3-MeOH (30:1, v/v) as eluent to afford 1.18 g (100%) methyl 4-[N-[1-[3-methoxy4-[N′-(2-fluorophenyl)ureido]phenylacetyl]-2-pyrrolidinyl methyl]-N-methylamino]-3-nitrobenzoate as a yellow foam, which is used to the subsequent reaction without further purification.

후처리

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed under a reduced pressure
  4. customthe residue was chromatographed on silica-gel with CHCl3-MeOH (30:1

출처 및 근거

ORD 기록
ord-fb623a385acd471e8992840f936a25a5
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

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