Triethylamine → HCID 46199086, compound

HRID 1959341Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:19](O)=O)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:6][N:7]=1.[CH3:22][NH:23][C:24]1[C:25]([NH2:30])=[CH:26][CH:27]=[CH:28][CH:29]=1.C(OP(C#N)(OCC)=O)C.C(N(CC)CC)C>COCCOC>[CH2:17]([S:14]([N:11]1[CH2:12][CH2:13][N:8]([C:5]2[N:4]=[C:3]([C:19]3[N:23]([CH3:22])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[N:30]=3)[C:2]([NH2:1])=[N:7][CH:6]=2)[CH2:9][CH2:10]1)(=[O:16])=[O:15])[CH3:18]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 3-amino-6-(4-ethylsulfonylpiperazin-1-yl)pyrazine-2-carboxylic acid (100 mg, 0.3171 mmol), N-methylbenzene-1,2-diamine (42.61 mg, 39.64 μL, 0.3488 mmol), diethoxyphosphorylformonitrile (56.89 mg, 51.72 μL, 0.3488 mmol) and triethylamine (64.17 mg, 88.39 μL, 0.6342 mmol) in DME (3.000 mL) was heated in the microwave at 150° C. for 20 mins. The reaction mixture was allowed to cool and concentrated in vacuo. The resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as a yellow solid (79 mg, 60% Yield).

Workup

temperatureto cool
concentrationconcentrated in vacuo
customThe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
customThe fractions were collected
customfreeze-dried

Sources & evidence

ORD record: ord-ea77b7403198415e987ef57de910ee8d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

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