Diisopropylethylamine → 4-(3-(4-(trifluoromethyl)phenoxy)benzylidene)-N-(3,4-dimethylisoxazol-5-yl)piperidine-1-carboxamide

HRID 1666428노트

반응식

HRID 1666428 반응식
Cl.[F:2][C:3]([F:25])([F:24])[C:4]1[CH:23]=[CH:22][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:6][CH:5]=1.[CH3:26][C:27]1[C:31]([CH3:32])=[C:30]([NH:33][C:34](=O)[O:35]C2C=CC=CC=2)[O:29][N:28]=1.NC1ON=C(C)C=1C.C(N(C(C)C)CC)(C)C>C(#N)C>[F:25][C:3]([F:2])([F:24])[C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16]([C:34]([NH:33][C:30]3[O:29][N:28]=[C:27]([CH3:26])[C:31]=3[CH3:32])=[O:35])[CH2:15][CH2:14]2)=[CH:22][CH:23]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 883175-Amino-3,4-dimethylisoxazoleHCID 53485970Phenyl (3,4-dimethylisoxazol-5-yl)carbamateHCID 66875732HCID 66875732, 화합물

생성물 1

HCID 249651424-(3-(4-(trifluoromethyl)phenoxy)benzylidene)-N-(3,4-dimethylisoxazol-5-yl)piperidine-1-carboxamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

4-(3-(4-(Trifluoromethyl)phenoxy)benzylidene)piperidine hydrochloride (200 mg, 0.541 mmol, from Example 53, Step 5), phenyl 3,4-dimethylisoxazol-5-ylcarbamate (126 mg, 0.541 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 5-amino-3,4-dimethylisoxazole) and diisopropylethylamine (0.20 mL, 1.15 mmol) were combined in acetonitrile (5 mL) and stirred at room temperature. After 16 h, the reaction was concentrated and the residue was purified by silica gel chromatography (0-30% EtOAc:CH2Cl2) to afford the title compound (218 mg) as a white solid. MS APCI M+ 472.3, 431.2, 375.3, 334.2; 1H NMR (400 MHz, CD3OD) δ ppm 1.83 (s, 3H) 2.18 (s, 3H) 2.44 (td, J=5.77, 1.07 Hz, 2H) 2.54 (td, J=5.81, 1.16 Hz, 2H) 3.49-3.54 (m, 2H) 3.59-3.63 (m, 2H) 6.44 (s, 1H) 6.90-6.98 (m, 2H) 7.05-7.14 (m, 3H) 7.35-7.44 (m, 1H) 7.59-7.67 (m, 2H).

후처리

  1. concentrationthe reaction was concentrated
  2. customthe residue was purified by silica gel chromatography (0-30% EtOAc:CH2Cl2)

출처 및 근거

ORD 기록
ord-4c6edbbcdebe44e6821b524fd9183d84
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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