Dimethylamine → HCID 67236391, compound

HRID 83845Notes

Reaction equation

CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([CH2:16][S:17][C:18]2[N:19]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[C:20]([C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([O:33][CH3:34])[CH:27]=3)([CH3:25])[CH3:24])=[CH:21][N:22]=2)=[C:11]([F:42])[CH:10]=1)(=O)=O.[CH3:43][NH:44][CH3:45].C(NC(C)C)(C)C.CN(C=O)C>CCOC(C)=O>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([C:23]([C:20]2[N:19]([C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)[C:18]([S:17][CH2:16][C:12]3[C:13]([F:15])=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:44]([CH3:45])[CH3:43])=[CH:10][C:11]=3[F:42])=[N:22][CH:21]=2)([CH3:25])[CH3:24])=[CH:27][C:28]=1[O:33][CH3:34]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-(4-((5-(2-(4-Chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethyl methanesulfonate (230 mg, 0.36 mmol, 1.0 eq), dimethylamine (7.2 mL, 14.4 mmol, 40.0 eq, 2.0 M in THF) and diisopropylamine (0.2 mL, 1.1 mmol, 3.0 eq) in anhyd DMF (3.5 mL) was heated at 110° C. for 16 h. The mixture was diluted with EtOAc, washed sequentially with brine, satd NaHCO3 and brine, dried over MgSO4 and concentrated to provide 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)-N,N-dimethylethanamine (187 mg). 1H NMR (400 MHz, CDCl3) δ 7.13 (s, 1H), 7.07 (d, J=8.2 Hz, 1H), 6.72-6.65 (m, 2H), 6.48-6.40 (m, 2H), 6.34-6.25 (m, 4H), 3.98-3.92 (m, 4H), 3.68 (s, 3H), 2.68 (t, J=5.5 Hz, 2H), 2.28 (s, 3H), 1.41 (s, 6H); MS (EI) m/z 590 (MH+).

Workup

washwashed sequentially with brine
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-1fc063d4044848ecbcb6dbba82c6c9ee
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846739B2

Reaction notes

Loading…