Cesium carbonate → HCID 178432958, compound

HRID 877390Notes

Reaction equation

HRID 877390 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][CH:14]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)[C:15]3[N:16]=[C:17]([CH3:20])[NH:18][CH:19]=3)=[O:12])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[C:28]([O-:31])([O-])=O.[Cs+].[Cs+].FC(F)(F)S(O[CH2:40][C:41]([F:44])([F:43])[F:42])(=O)=O>>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH2:10][C:11]([NH:13][C:14]([C:1]3[CH:4]=[CH:5][C:28]([OH:31])=[CH:3][CH:2]=3)([C:15]3[N:16]=[C:17]([CH3:20])[NH:18][CH:19]=3)[C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:40][C:41]([F:44])([F:43])[F:42])=[CH:23][CH:22]=3)=[O:12])=[CH:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 178432959HCID 178432959, compound

Product 1

HCID 178432958HCID 178432958, compoundYield 74.7%

Procedure

To a 5 ml round bottom flask containing solution of 2-(4-cyclopropylphenyl)-N-[(4-hydroxyphenyl)(2-methyl-1H-imidazol-4-yl)methyl]acetamide (10.00 mg, 0.0280 mmol) in 0.3 ml of CH2Cl at RT was added Cs2CO3 (18.03 mg, 0.0550 mmol). To the mixture was added dropwise 2,2,2-trifluoroethyl trifluoromethanesulfonate (6.420 mg, 0.0280 mmol). The resulting solution was stirred at RT for 16 hours. Filtered and the filtrate was purified by preparative HPLC (10-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 5.60 mg (46%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.448 (d, J=7.32 Hz, 1H), 7.152 (d, J=8.60 Hz, 2H), 7.071 (d, J=8.06 Hz, 2H), 6.936 (d, J=8.05 Hz, 2H), 6.874 (d, J=8.61 Hz, 2H), 6.592 (s, 1H), 6.109 (d, J=7.88 Hz, 1H), 4.308 (q, J=8.06 Hz, 2H), 3.544 (s, 2H), 2.395 (s, 3H), 1.798 (m, 1H), 0.918 (m, 2H), 0.590 (m, 2H). ES-MS [M+1]+: 444.2.

Workup

  1. filtrationFiltered
  2. customthe filtrate was purified by preparative HPLC (10-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column)

Sources & evidence

ORD record
ord-62052f5de7fa455d890e3aa6330a16ee
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

Loading…