Diisopropylethylamine → HCID 118115233, compound

HRID 1050620Notes

Reaction equation

HRID 1050620 reaction equation
[NH2:1][C@@H:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH2:3]1.CCN(C(C)C)C(C)C.[Cl:23][C:24]1[C:25]([C:31]#[N:32])=[N:26][CH:27]=[C:28](Cl)[N:29]=1>C1COCC1>[Cl:23][C:24]1[N:29]=[C:28]([NH:1][C@@H:2]2[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH2:3]2)[CH:27]=[N:26][C:25]=1[C:31]#[N:32]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 529877443,5-Dichloropyrazine-2-carbonitrileHCID 118114513HCID 118114513, compound

Product 1

HCID 118115233HCID 118115233, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-3-Amino-N,N-dimethylazepane-1-carboxamide (508) (˜200 mg crude) was dissolved in THF (7 mL), and DIEA (0.30 mL, 1.7 mmol) was added, followed by 3,5-dichloropyrazine-2-carbonitrile (100 mg, 0.57 mmol). The reaction was stirred at RT for 12 hours. The solvents were removed under reduced pressure, and the residue was purified by silica column chromatography (MeOH, DCM) to give (R)-3-(6-chloro-5-cyanopyrazin-2-ylamino)-N,N-dimethylazepane-1-carboxamide (509) (53 mg, 0.16 mmol, 14% yield over 3 steps).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was purified by silica column chromatography (MeOH, DCM)

Sources & evidence

ORD record
ord-ec45a311976e4137a87757cfab9492f4
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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