Diisopropylethylamine → 4-({3-Chloro-4-[-2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzoyl}-methyl-amino)-benzoic acid methyl ester

HRID 1095884노트

반응식

HRID 1095884 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH:11]([CH3:25])[C:12]([C:18]1[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[CH:19]=1)([OH:17])[C:13]([F:16])([F:15])[F:14])[C:5](O)=[O:6].[CH3:26][O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([NH:35][CH3:36])=[CH:31][CH:30]=1.C(N(C(C)C)C(C)C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl>[CH3:26][O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([N:35]([C:5](=[O:6])[C:4]2[CH:8]=[CH:9][C:10]([CH:11]([CH3:25])[C:12]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[CH:19]=3)([OH:17])[C:13]([F:16])([F:14])[F:15])=[C:2]([Cl:1])[CH:3]=2)[CH3:36])=[CH:31][CH:30]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 140375Methyl 4-methylaminobenzoateHCID 2733179PyBroPHCID 57421268HCID 57421268, 화합물

생성물 1

HCID 469410034-({3-Chloro-4-[-2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzoyl}-methyl-amino)-benzoic acid methyl ester수율 34.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzoic acid (Example 26, step 3, 80 mg, 0.2 mmol) and 4-methylamino-benzoic acid methylester (35 mg, 0.21 mmol) in dichloromethane (4 ml) were added N-ethyldiisopropylamine (29 mg, 0.22 mmol) and PyBroP (95 mg, 0.2 mmol). The mixture was stirred for 17 h at room temperature. The reaction solution was extracted with brine/water, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (5 g silica gel, heptane/AcOEt 8:2=>7:3) to give the title compound (37 mg) as a white solid. MS (m/e)=541.3 [M+H+].

후처리

  1. extractionThe reaction solution was extracted with brine/water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (5 g silica gel, heptane/AcOEt 8:2=>7:3)

출처 및 근거

ORD 기록
ord-dc6c70980c244159a679803b2de54c85
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138189B2

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