1,2-Dichloroethane → Hydrochloric Acid

HRID 888399Notes

Reaction equation

[CH:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:12]=1)[C:7]([OH:9])=O)([CH3:3])[CH3:2].[N:20]1[N:21]=[C:22]([C@@H:25]([NH2:27])[CH3:26])[NH:23][CH:24]=1.C(Cl)C[Cl:30].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.FC(F)(F)C(O)=O>CN(C)C=O.O>[ClH:30].[CH:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:12]=1)[C:7]([NH:27][C@H:25]([C:22]1[NH:23][CH:24]=[N:20][N:21]=1)[CH3:26])=[O:9])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 3-isopropyl-5-(5-methylpyridin-2-yl)benzoic acid (100 mg, 0.392 mmol) in N,N-dimethylformamide (3.0 mL) was added the hydrochloride salt of (1S)-1-(4H-1,2,4-triazol-3-yl)ethanamine (107 mg, 0.578 mmol), EDC (90.0 mg, 0.470 mmol), HOBT (60.0 mg, 0.392 mmol) and triethylamine (0.164 mL, 1.175 mmol) and the mixture was heated to 45° C. After 1 h, water and trifluoroacetic acid were added. The mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid). Treatment with 2 M hydrochloric acid in diethyl ether gave the title compound as a hydrochloride salt (153 mg). HRMS 350.1976 (M+1). 1H NMR (500 MHz, CD3OD): δ 9.21 (s, 1H); 8.73 (s, 1H); 8.55 (d, J=8.4 Hz, 1H); 8.36 (d, J=8.4 Hz, 1H); 8.30 (s, 1H); 8.12 (s, 1H); 8.01 (s, 1H); 5.52 (q, J=7.1 Hz, 1H); 3.20-3.12 (m, 1H); 2.63 (s, 3H); 1.79 (d, J=7.1 Hz, 3H); 1.39 (d, J=6.9 Hz, 6H).

Workup

customThe mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-2b74274a11da4d2f8082cbc819235ce2
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247401B2

Reaction notes

Loading…