Hydrochloric Acid → HCID 118092787, compound

HRID 2207359Notes

Reaction equation

HRID 2207359 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:20]=[CH:21][C:22]([CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])=[N:23][CH:24]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.Cl.O1CCOCC1>>[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:20]=[CH:21][C:22]([CH2:25][C:26]([OH:28])=[O:27])=[N:23][CH:24]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:12]=[CH:11][N:10]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131735889HCID 131735889, compound

Product 1

HCID 118092787HCID 118092787, compoundYield 58.9%

Procedure

tert-Butyl 2-(5-(3-methyl-5-((4-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)pyridin-2-yl)acetate (25 mg, 0.056 mmol) was added to HCl in dioxane (0.5 ml, 2.000 mmol, 4M). The mixture was stirred at room temperature for 1 hour. The solid was collected by the filtration and afforded 2-(5-(3-methyl-5-((4-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)pyridin-2-yl)acetic acid (14.1 mg, 0.033 mmol). MS ESI calc'd. for C19H16F3N4O2 [M+H]+ 389. found 389. 1H NMR (500 MHz, CD3OD): δ 9.07 (d, J=1.5 Hz, 1H), 8.83 (dd, J=8.0, 1.5 Hz, 1H), 8.73 (d, J=5.0 Hz, 1H), 8.15-8.10 (m, 2H), 7.66 (s, 1H), 7.34 (s, 1H), 7.18 (d, J=5.0 Hz, 1H), 4.25 (s, 2H), 2.46 (s, 3H).

Workup

  1. filtrationThe solid was collected by the filtration

Sources & evidence

ORD record
ord-c03187bf3c074d70a47b70eb6cb1dac1
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

Loading…