1,2-Dichloroethane → N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)-N-methylpiperidine-4-carboxamide

HRID 1025400노트

반응식

HRID 1025400 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:23])=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]3)[N:12]=2)=[CH:4][CH:3]=1.[N:24]1([CH2:31][CH2:32][CH2:33][NH:34][CH3:35])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[N:24]1([CH2:31][CH2:32][CH2:33][N:34]([CH3:35])[C:20]([CH:17]2[CH2:18][CH2:19][N:14]([CH2:13][C:11]3[N:12]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[O:9][C:10]=3[CH3:23])[CH2:15][CH2:16]2)=[O:22])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 206007003-(Azepan-1-yl)-N-methylpropan-1-amineHCID 209671331-((2-(4-Chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

생성물 1

HCID 45280367N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)-N-methylpiperidine-4-carboxamide수율 82%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid (A-3, 70 mg, 0.52 mmole), 3-(azepan-1-yl)-N-methylpropan-1-amine (20 mg) and DIPEA (0.05 mL) in DMF (2 mL) was added EDC (35 mg). The reaction solution was stirred at room temperature for 12 hours. The reaction was diluted with EtOAc (30 mL). The organic layer was washed with saturated sodium bicarbonate (10 mL), water (10 mL) and dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified through chromatography (CH2Cl2:MeOH 10:1) to give N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)-N-methylpiperidine-4-carboxamide (42 mg, 82%). H1NMR (300 MHz, CDCl3), ppm: 7.97 (d, 2H), 7.48 (d, 2H), 3.80 (m, 1H), 3.63 (m, 2H), 3.45 (m, 2H), 3.31-3.14 (m, 7H), 2.75 (s, 3H), 2.44 (m, 4H), 2.01 (m, 2H), 1.85 (m, 10H), 1.30 (m, 2H), 1.26 (m, 2H). MS (ESI+) M/z: 487, 489 (M+H).

후처리

  1. washThe organic layer was washed with saturated sodium bicarbonate (10 mL), water (10 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified through chromatography (CH2Cl2:MeOH 10:1)

출처 및 근거

ORD 기록
ord-7d7fa4203dab4a30825dd48bfeee0467
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729081B2

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