Diethyl Ether → (1-benzyl-1H-indazol-5-yl)-(4-chloro-[1,3,5]triazin-2-yl)amine

HRID 1815913Notes

Reaction equation

ClN1C=[C:6]([Cl:8])[N:5]=[CH:4][NH:3]1.C[CH2:10][N:11](C(C)C)C(C)C.[CH2:18]([N:25]1[C:33]2[C:28](=[CH:29][C:30]([NH2:34])=[CH:31][CH:32]=2)[CH:27]=[N:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCOCC>CN(C=O)C.CCOC(C)=O>[CH2:18]([N:25]1[C:33]2[C:28](=[CH:29][C:30]([NH:34][C:10]3[N:11]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=3)=[CH:31][CH:32]=2)[CH:27]=[N:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 2,4-dichloro-1,2,5-triazine (526.1 mg, 3.51 mmol) in DMF (15 mL) at O2C was added DIEA (0.733 mL, 4.21 mmol). The resulting yellow solution was stirred at 0° C. for 20 min and 1-benzyl-1H-indazol-5-ylamine (Step 2) (783.5 mg, 3.51 mmol) was added in one portion followed by 2×2.5 mL DMF flask rinses. The resulting mixture was stirred at 0° C. for 30 min, at RT for 4.5 h, then diluted with EtOAc. The organic layer was washed twice with water and once with brine. The aqueous layer and washings were extracted with EtOAc. The combined organics were dried, concentrated, and purified by chromatography (SiO2, elution with 1:1 EtOAc-hexanes) to give a slightly impure pinkish solid. Trituration with Et2O gave (1-benzyl-1H-indazol-5-yl)-(4-chloro-[1,3,5]triazin-2-yl)amine as a light pink solid: MS m/z=337 [M+H]+. Calc'd for C17H13ClN6: 336.09.

Workup

stirringThe resulting mixture was stirred at 0° C. for 30 min, at RT for 4.5 h
washThe organic layer was washed twice with water and once with brine
extractionThe aqueous layer and washings were extracted with EtOAc
customThe combined organics were dried
concentrationconcentrated
custompurified by chromatography (SiO2, elution with 1:1 EtOAc-hexanes)
customto give a slightly impure pinkish solid

Sources & evidence

ORD record: ord-906c9b8f6b7e40708aefcea9db54448c
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881737B2

Reaction notes

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