Triethylamine → HCID 86666582, compound

HRID 2088929Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([CH2:9][C:10]([F:13])([F:12])[F:11])[N:6]=[C:5]1[CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:21]3[C@H:29]([C:30]([F:33])([F:32])[F:31])[CH2:28][C:27](=[O:34])[NH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH2:16][CH2:15]1.C(N(CC)CC)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>ClCCl>[CH3:42][S:43]([O:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([CH2:9][C:10]([F:12])([F:11])[F:13])[N:6]=[C:5]1[CH:14]1[CH2:15][CH2:16][N:17]([C:20]2[C:21]3[C@H:29]([C:30]([F:33])([F:32])[F:31])[CH2:28][C:27](=[O:34])[NH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH2:18][CH2:19]1)(=[O:45])=[O:44]

Participants

Conditions

Temperature: 0 °C

Procedure

Combine (R)-4-(4-(1-(2-hydroxyethyl)-4-(2,2,2-trifluoroethyl)-1H-imidazol-2-yl)piperidin-1-yl)-5-(trifluoromethyl)-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one (0.93 g, 1.88 mmol), dichloromethane (14 mL), and triethylamine (0.79 mL, 3.0 eq). Place under nitrogen and cool to 0° C. Add methanesulfonyl chloride (0.17 mL, 1.2 eq) dropwise. After 30 minutes, dilute with dichloromethane and quench with saturated aqueous sodium bicarbonate. Separate the layers. Dry the organics over anhydrous sodium sulfate, filter, and concentrate in vacuo to give (R)-2-(2-(1-(7-oxo-5-trifluoromethyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-4-yl)piperidin-4-yl)-4-(2,2,2-trifluoroethyl)-1H-imidazol-1-yl)ethyl methanesulfonate as a yellow solid (1.07 g, 96%). MS (ES) m/z=571 [M]+.

Workup

customquench with saturated aqueous sodium bicarbonate
customSeparate the layers
dry with materialDry the organics over anhydrous sodium sulfate
filtrationfilter
concentrationconcentrate in vacuo

Sources & evidence

ORD record: ord-bfa96ffca63242739930fa064ef56d23
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436002B2

Reaction notes

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