1,2-Dichloroethane → Hydrochloric Acid

HRID 888404ノート

反応式

HRID 888404 の反応式
[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

参加物

10

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-82364f7e033646df9a210e29190a7ef3
出典データセット
uspto-grants-2012_08
特許番号
US08247401B2

反応ノート

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