Ammonia → N-(3-{1-[(3R)-3-(3,4-Dichlorophenoxy)-3-Phenylpropyl]-4-Piperidinyl}Phenyl)-2-Methylpropanamide

HRID 1832180노트

반응식

HRID 1832180 반응식
[OH:1][C@H:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1.[Cl:29][C:30]1[CH:31]=[C:32](O)[CH:33]=[CH:34][C:35]=1[Cl:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.N>C1COCC1.C(Cl)(Cl)Cl>[Cl:29][C:30]1[CH:31]=[C:32]([CH:33]=[CH:34][C:35]=1[Cl:36])[O:1][C@@H:2]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1

참가 물질

8

반응물 5

HCID 222AmmoniaHCID 72583,4-DichlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 60078700N-(3-{1-[(3S)-3-Hydroxy-3-Phenylpropyl]-4-Piperidinyl}Phenyl)-2-Methylpropanamide

생성물 1

HCID 60078689N-(3-{1-[(3R)-3-(3,4-Dichlorophenoxy)-3-Phenylpropyl]-4-Piperidinyl}Phenyl)-2-Methylpropanamide수율 39.7%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of N-(3-{1-[(3S)-3-hydroxy-3-phenylpropyl]-4-piperidinyl}phenyl)-2-methylpropanamide (9.53 mg, 0.0250 mmol), 3,4-dichlorophenol (8.20 mg, 0.050 mmol), triphenylphosphine (9.80 mg, 0.0375 mmol) and diethyl azodicarboxylate (5.22 mg, 0.0300 mmol) in THF (1.0 mL) was stirred at room temperature for 3 days. Chromatography using silica preparative TLC plates [2.5% of NH3 (2.0 M in methanol) in CHCl3] gave the desired product (5.20 mg, 39.7% yield) as a thick oil: 1H NMR (CDCl3) δ 7.70–7.63 (m, 2H), 7.55 (m, 1H), 7.47–7.43 (m, 3H), 7.40–7.19 (m, 3H), 7.00–6.50 (m, 2H), 6.69 (dd, 1H, J=2.2, 8.8 Hz), 5.25 (m, 1H), 3.20 (m, 2H), 2.70 (m, 2H), 2.53 (m, 2H), 2.40–2.20 (m, 4H), 2.10–1.80 (m, 4H), 1.25 (d, 6H, J=7, 1 Hz); ESMS m/e: 525.4 (M+H)+.

출처 및 근거

ORD 기록
ord-5bf352c9516c482c831de7aebb8456db
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067534B1

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