Triethylamine → N-(cyanomethyl)-4-methyl-2-[(5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]pentanamide

HRID 1744081Notes

Reaction equation

HRID 1744081 reaction equation
[CH3:1][CH:2]([CH3:20])[CH2:3][CH:4]([S:8][C:9]1[NH:13][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:11][N:10]=1)[C:5]([OH:7])=O.Cl.[NH2:22][CH2:23][C:24]#[N:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.O>[C:23]([CH2:24][NH:25][C:5](=[O:7])[CH:4]([S:8][C:9]1[NH:13][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:11][N:10]=1)[CH2:3][CH:2]([CH3:1])[CH3:20])#[N:22]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11491918Aminoacetonitrile hydrochlorideHCID 178447703HCID 178447703, compound

Product 1

HCID 178447702N-(cyanomethyl)-4-methyl-2-[(5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]pentanamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the crude 4-methyl-2-[(5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]pentanoic acid in DMF (10 mL) was added aminoacetonitrile hydrochloride (427 mg, 4.62 mmoles) and HATU (1.76 g, 4.62 mmoles). After stirring for 30 seconds, triethylamine (1.3 mL, 9.24 mmoles) was added in one portion. The reaction was stirred overnight, diluted with ethyl acetate and water. The organic phase was separated and washed twice with 1.2 N hydrochloric acid, brine and dried over magnesium sulfate. After concentration under reduced pressure, N-(cyanomethyl)-4-methyl-2-[(5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]pentanamide was obtained. MS (−APCI): 328.2 [M−1]−.

Workup

  1. stirringThe reaction was stirred overnight
  2. customThe organic phase was separated
  3. washwashed twice with 1.2 N hydrochloric acid, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationAfter concentration under reduced pressure

Sources & evidence

ORD record
ord-055a2a26353e4571b1aa93e01494c5f9
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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