Ammonium Chloride → 2-{3-[2-(Trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxamide

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[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:16]([OH:18])=O)=[CH:14][N:15]=2)[CH2:7]1.C1C=CC2N(O)N=[N:31]C=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH4+].[Cl-].CCN(C(C)C)C(C)C>CN(C=O)C>[F:23][C:2]([F:24])([F:1])[C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:16]([NH2:31])=[O:18])=[CH:14][N:15]=2)[CH2:7]1

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실험 절차

To a solution of 2-{3-[2-(trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxylic acid (860 mg, 2.4 mmol), HOBt (324 mg, 2.4 mmol), HATU (1.5 g, 3.8 mmol) and NH4Cl (385 mg, 7.2 mmol) in DMF at rt was added DIPEA (2.1 mL, 12 mmol). The mixture was stirred at rt overnight. After dilution with water, the mixture was extracted twice with EtOAc. The EtOAc extracts were combined, washed twice with 0.5 N NaOH, diluted brine, dried (Na2SO4) and concentrated. The residue was triturated with Et2O:hexanes (1:1) to give the title compound as a pale yellow solid. 1H NMR (500 MHz, acetone-d6): δ 7.79 (s, 1 H), 7.68-7.64 (m, 2 H), 7.39 (d, 1 H), 7.15 (t, 1 H), 5.48 (s, 1 H), 3.91 (m, 1 H), 3.78-3.62 (m, 4 H), 2.57-2.49 (m, 1 H), 2.44-2.40 (m, 1 H). MS (+ESI) m/z 358 (MH+).

후처리

extractionAfter dilution with water, the mixture was extracted twice with EtOAc
washwashed twice with 0.5 N NaOH, diluted brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue was triturated with Et2O:hexanes (1:1)

출처 및 근거

ORD 기록: ord-62f70e8fa56c4ad78097c13c1e24fff9
출처 데이터셋: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07754745B2

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