Diisopropylethylamine → N2-[(1S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl]-N1-(l-cyanocyclopropyl)-L-leucinamide

HRID 1880512Notes

Reaction equation

HRID 1880512 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C@H:8]([NH:13][C@H:14]([C:19]([OH:21])=O)[CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.Cl.[NH2:23][C:24]1([C:27]#[N:28])[CH2:26][CH2:25]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.O.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C@H:8]([NH:13][C@H:14]([C:19]([NH:23][C:24]2([C:27]#[N:28])[CH2:26][CH2:25]2)=[O:21])[CH2:15][CH:16]([CH3:17])[CH3:18])[C:9]([F:10])([F:11])[F:12])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 86590542N-[(1S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl]-L-leucine

Product 1

HCID 59715496N2-[(1S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl]-N1-(l-cyanocyclopropyl)-L-leucinamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the crude acid (0.73 g, 2.25 mmol) from Step 2 in DMF (12 mL) was added 1-aminocyclopropanecarbonitrile hydrochloride (0.4 g, 3.37 mmol.) and HATU (0.86 g, 2.25 mmol). Diisopropylethylamine (1.96 mL, 11.24 mmol) was added, the mixture was stirred at rt for 20 h. EtOAc and water were added. The mixture was separated after agitation and the organic extract was washed with water and brine and dried over anhyd. MgSO4. Concentration of the organic extract followed by chromatography (30-50% EtOAc/hexane) gave the title compound.

Workup

  1. customThe mixture was separated after agitation
  2. extractionthe organic extract
  3. washwas washed with water and brine
  4. customdried over anhyd
  5. extractionConcentration of the organic extract

Sources & evidence

ORD record
ord-ac562651857c47c38a28f094eb3fac7f
Source dataset
uspto-grants-2012_11
Patent number
US08318748B2

Reaction notes

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