1,2-Dichloroethane → Hydrochloric Acid

HRID 888404노트

반응식

HRID 888404 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([C:15]([OH:18])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:19](O)=[O:20])[CH:10]=1.[CH3:22][C:23]1[N:27]=[C:26]([C@H:28]([NH2:30])[CH3:29])[O:25][N:24]=1.C(Cl)C[Cl:33].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.FC(F)(F)C(O)=O>CN(C)C=O.O>[ClH:33].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([C:15]([OH:18])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:19]([NH:30][C@@H:28]([C:26]2[O:25][N:24]=[C:23]([CH3:22])[N:27]=2)[CH3:29])=[O:20])[CH:10]=1

참가 물질

10

반응물 6

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 28948822(R)-1-(3-Methyl-1,2,4-oxadiazol-5-yl)ethan-1-amineHCID 685009892',4'-Difluoro-5-(1-hydroxy-1-methylethyl)biphenyl-3-carboxylic acid

생성물 2

HCID 313Hydrochloric AcidHCID 426030322',4'-Difluoro-5-(1-hydroxy-1-methylethyl)-N-[(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]biphenyl-3-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2′,4′-difluoro-5-(1-hydroxy-1-methylethyl)biphenyl-3-carboxylic acid (34 mg, 0.116 mmol) in N,N-dimethylformamide (1.2 mL) was added the hydrochloride salt of (1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine, EDC (26.8 mg, 0.140 mmol), HOBT (17.8 mg, 0.116 mmol) and triethylamine (0.065 mL, 0.465 mmol). After 16 h, water and trifluoroacetic acid were added. The mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid). Treatment with 2 M hydrochloric acid in diethyl ether gave the title compound as a hydrochloride salt (50.1 mg). HRMS 402.1633 (M+1). 1H NMR (500 MHz, CD3OD): δ 8.03 (t, J=1.8 Hz, 1H); 7.89-7.86 (m, 2H); 7.58 (q, J=7.6 Hz, 1H); 7.12-7.07 (m, 2H); 5.46 (q, J=7.1 Hz, 1H); 2.37 (s, 3H); 1.71 (d, J=7.1 Hz, 3H); 1.61 (s, 6H).

후처리

  1. customThe mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-82364f7e033646df9a210e29190a7ef3
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247401B2

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