Diisopropylethylamine → HCID 86685607, compound

HRID 2200490Notes

Reaction equation

HRID 2200490 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@@H:13]([C:17]([NH2:19])=[O:18])[CH:14]([CH3:16])[CH3:15].CCN(C(C)C)C(C)C>C(C#N)(C)=O.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:12][C@H:13]([CH:14]([CH3:16])[CH3:15])[C:17]([NH2:19])=[O:18])[CH:5]=[N:4][C:3]=1[C:9]#[N:10]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 529877443,5-Dichloropyrazine-2-carbonitrileHCID 53486046(2R)-2-amino-3-methylbutanamide hydrochloride

Product 1

HCID 86685607HCID 86685607, compoundYield 102.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 694302-OxopropiononitrileSolvent

Procedure

To a mixture of 3,5-dichloropyrazine-2-carbonitrile (500 mg, 2.84 mmol) and D-valinamide HCl salt (476 mg, 3.12 mmol) in AcCN (10 mL) was added DIPEA (1.11 mL, 6.25 mmol). After stirring at room temperature for 4 h, it was diluted with EtOAc, washed with sat. NaHCO3, organic layer was separated and washed with brine, dried and concentrated to give (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-methylbutanamide (740 mg).

Workup

  1. washwashed with sat. NaHCO3, organic layer
  2. customwas separated
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-830d15457a8440c78c986261d96efdfc
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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