Diisopropylethylamine → (R)-benzyl-1-((6-chloro-5-cyanopyrazin-2-ylamino)(cyclopropyl)methyl)cyclopropylcarbamate

HRID 332817Notes

Reaction equation

HRID 332817 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]([CH:28]1[CH2:30][CH2:29]1)[C:14]1([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1.CCN(C(C)C)C(C)C>C(C#N)(C)=O.CCOC(C)=O>[CH2:20]([O:19][C:18](=[O:27])[NH:17][C:14]1([C@H:13]([NH:12][C:6]2[CH:5]=[N:4][C:3]([C:9]#[N:10])=[C:2]([Cl:1])[N:7]=2)[CH:28]2[CH2:29][CH2:30]2)[CH2:15][CH2:16]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 529877443,5-Dichloropyrazine-2-carbonitrileHCID 131732000(R)-benzyl 1-(amino(cyclopropyl)methyl)cyclopropylcarbamate HCl salt

Product 1

HCID 86685610(R)-benzyl-1-((6-chloro-5-cyanopyrazin-2-ylamino)(cyclopropyl)methyl)cyclopropylcarbamateYield 101.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 694302-OxopropiononitrileSolvent

Procedure

To a mixture of 3,5-dichloropyrazine-2-carbonitrile (208 mg, 1.19 mmol) and (R)-benzyl 1-(amino(cyclopropyl)methyl)cyclopropylcarbamate HCl salt (350 mg, 1.19 mmol) in AcCN (2 mL) was added DIPEA (0.467 mL, 2.62 mmol). After stirring at room temperature for 3 h, it was diluted with EtOAc, washed with sat. NaHCO3, organic layer was separated and washed with brine, dried and concentrated to give (R)-benzyl-1-((6-chloro-5-cyanopyrazin-2-ylamino)(cyclopropyl)methyl)cyclopropylcarbamate (480 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-ff139d9556c2474dbcd8d63c1d8f610a
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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