1,2-Dichloroethane → N-[(1R)-1-(5-bromo-1,3-thiazol-2-yl)ethyl]-2-[4-(propan-2-yl)phenyl]acetamide

HRID 877366

反応式

HRID 877366 の反応式
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl.[Br:15][C:16]1[S:20][C:19]([C@H:21]([NH2:23])[CH3:22])=[N:18][CH:17]=1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Br:15][C:16]1[S:20][C:19]([C@H:21]([NH:23][C:11](=[O:13])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:9][CH:8]=2)[CH3:22])=[N:18][CH:17]=1

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 782304-Isopropylphenylacetic acidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 68156351(1R)-1-(5-bromo-1,3-thiazol-2-yl)ethanamine hydrochloride

生成物 1

HCID 69932452N-[(1R)-1-(5-bromo-1,3-thiazol-2-yl)ethyl]-2-[4-(propan-2-yl)phenyl]acetamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.050 g (0.28 mmol) 4-isopropylphenyl acetic acid in 0.50 mL DMF and 1.0 mL CH2Cl2 was added 0.072 g (0.30 mmol) (1R)-1-(5-bromo-1,3-thiazol-2-yl)ethanamine hydrochloride, 0.042 g (0.31 mmol) HOAT, 0.059 g (0.31 mmol) EDC, and 0.093 mL (0.56 mmol) DIEA. After 1 h at room temperature, the reaction mixture was purified by preparative reverse-phase HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18) to give N-[(1R)-1-(5-bromo-1,3-thiazol-2-yl)ethyl]-2-[4-(propan-2-yl)phenyl]acetamide. 1H NMR (CDCl3, 400 MHz) δ 7.54 (s, 1H); 7.59 (ABq, J=8.4 Hz, 4H), 6.55 (br d, J=7.6 Hz, 1H), 5.32 (quintet, J=7.2 Hz, 1H), 3.59 (s, 2H), 2.91 (m, J=7.2 Hz, 3H); 1.52 (d, J=7.2 Hz, 3H), 1.25 (d, J=7.2 Hz, 6H). HRMS (ES) [M+1]+ calcd for C16H19BrN2OS: 367.0474. Found: 367.0483.

後処理

  1. customthe reaction mixture was purified by preparative reverse-phase HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18)

出典と根拠

ORDレコード
ord-910ab1a7cb984f70a107b865b8fa6a8e
出典データセット
uspto-grants-2015_03
特許番号
US08987310B2

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