Dimethylformamide → HCID 178473713, compound

HRID 2041787Notes

Reaction equation

[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]#[CH:15])=[CH:11][CH:12]=2)[C@H:7]([NH:16][C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:6][C@@H:5]1[CH3:23])(=[O:3])[CH3:2].CN(C)C=O.C[Si]([N:33]=[N+:34]=[N-:35])(C)C>[Cu]I.CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[N:33]=[N:34][NH:35][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:16][C:17]2[N:18]=[CH:19][CH:20]=[CH:21][N:22]=2)[CH2:6][C@@H:5]1[CH3:23])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A flask was charged with (2S,4R)-1-acetyl-6-ethynyl-2-methyl-N-2-pyrimidinyl-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 114) (45 mg, 0.147 mmol) and copper (I) iodide (2.80 mg, 0.015 mmol) then filled with N,N-dimethylformamide (DMF) (1.8 mL) and methanol (0.200 mL) and the resulting mixture was treated with trimethylsilyl azide (0.078 mL, 0.588 mmol). The flask was flushed with nitrogen then the mixture was stirred at 100° C. for 1 h under microwave irradiation then cooled to room temperature. Most of the methanol was removed in vacuo and the remaining organic phase was purified by MDAP (modifier: ammonium bicarbonate) to give (2S,4R)-1-acetyl-2-methyl-N-2-pyrimidinyl-6-(1H-1,2,3-triazol-4-yl)-1,2,3,4-tetrahydro-4-quinolinamine (3 mg, 8.59 μmol, 5.85% yield) as a colourless film.

Workup

customThe flask was flushed with nitrogen
temperaturethen cooled to room temperature
customMost of the methanol was removed in vacuo
customthe remaining organic phase was purified by MDAP (modifier: ammonium bicarbonate)

Sources & evidence

ORD record: ord-3c486b35d9dc43dc910bcf228180307f
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580957B2

Reaction notes

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