Diisopropylethylamine → 4-(4-Thiophen-3-yl-[1,3,5]triazin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 910667Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[C:18](Cl)[N:17]=[C:16]([C:21]3[CH:25]=[CH:24][S:23][CH:22]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C>CC(O)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:15]=[C:16]([C:21]3[CH:25]=[CH:24][S:23][CH:22]=3)[N:17]=[CH:18][N:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 4-(4-chloro-6-thiophen-3-yl-[1,3,5]triazin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (169 mg, 0.29 mmol) in 2-propanol/EtOAc (10:1, 11 mL) at room temperature was added DIEA (0.5 mL). The resulting solution was vacuum-flushed with N2 and then treated with 10% Pd/C (50 mg). The resulting suspension was exposed to H2 via balloon and heated to 65° C. After 3 h, 10% Pd/C (50 mg) was added, and the reaction mixture was heated at 65° C. overnight under H2. The resulting mixture was filtered to remove catalyst; the filtrate was concentrated and the residue was purified by preparative TLC (EtOAc/hexanes, 1:2) to yield a white solid.

Workup

customThe resulting solution was vacuum-flushed with N2
additiontreated with 10% Pd/C (50 mg)
addition10% Pd/C (50 mg) was added
temperaturethe reaction mixture was heated at 65° C. overnight under H2
filtrationThe resulting mixture was filtered
customto remove catalyst
concentrationthe filtrate was concentrated
customthe residue was purified by preparative TLC (EtOAc/hexanes, 1:2)
customto yield a white solid

Sources & evidence

ORD record: ord-73fb8145f6714d46ad4b034a9a9605cc
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022209B2

Reaction notes

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