Ethyl Acetate → HCID 67074115, compound

HRID 2093753Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.Cl[C:20]1[N:25]=[C:24]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])[N:23]=[C:22]([NH:32][C:33]2[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=2)[N:21]=1.CCOC(C)=O>C1COCC1>[OH:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH:1][C:20]2[N:25]=[C:24]([O:26][CH2:27][C:28]([F:31])([F:29])[F:30])[N:23]=[C:22]([NH:32][C:33]3[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=3)[N:21]=2)=[CH:4][CH:5]=1

Participants

Conditions

Temperature: 70 °C

Procedure

4-(aminomethyl)phenol (2.4 g) white solid and iPr2NEt (5.0 g) were added into a solution of methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (7.0 g) in THF (150 mL). The mixture was heated at 70° C. for 16 hours. After cooling, the mixture was charged with 250 mL of EtOAc. The resulting solution was washed with water (2×50 mL) and brine (30 mL). The organic layer was dried over MgSO4 and concentrated under vacuum to give a residue which was recrystallized in EtOAc to give 6.54 g of methyl 4-(4-(4-hydroxybenzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate.

Workup

temperatureAfter cooling
washThe resulting solution was washed with water (2×50 mL) and brine (30 mL)
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated under vacuum
customto give a residue which
customwas recrystallized in EtOAc

Sources & evidence

ORD record: ord-a65edc904ab448d4ac8458fffdc2cb0b
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445490B2

Reaction notes

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