Water → HCID 86685596, compound

HRID 2200479Notes

Reaction equation

HRID 2200479 reaction equation
[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](Cl)[N:7]=1.Cl.[NH2:12][C:13]1([C:17]([NH2:19])=[O:18])[CH2:16][CH2:15][CH2:14]1.CCN(C(C)C)C(C)C.O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:12][C:13]2([C:17]([NH2:19])=[O:18])[CH2:16][CH2:15][CH2:14]2)[CH:5]=[N:4][C:3]=1[C:9]#[N:10]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 529877443,5-Dichloropyrazine-2-carbonitrileHCID 717569071-aminocyclobutane-1-carboxamide hydrochloride

Product 1

HCID 86685596HCID 86685596, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,5-dichloropyrazine-2-carbonitrile (100 mg, 0.574 mmol), 1-aminocyclobutanecarboxamide hydrochloride (108 mg, 0.717 mmol) and DIEA (0.350 mL, 2.01 mmol) in DMF (4 mL) was stirred at room temperature for 70 h. Water and EtOAc were added. Organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give 1-(6-chloro-5-cyanopyrazin-2-ylamino)cyclobutanecarboxamide (22 mg).

Workup

  1. customOrganic phase was separated
  2. washwashed with 1N HCl
  3. dry with materialwith 5% NaHCO3, dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-9b932c5a0c204f47bdaa5045a8c95119
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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