Diisopropylethylamine → HCID 22236169, compound

HRID 1744151Notes

Reaction equation

HRID 1744151 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]([CH2:13][C:14]2([CH3:17])[CH2:16][CH2:15]2)[C:10]([OH:12])=O)=[CH:4][CH:3]=1.CN(C(O[N:26]1N=[N:33][C:28]2C=CC=N[C:27]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.NCC#N.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH:9]([CH2:13][C:14]2([CH3:17])[CH2:16][CH2:15]2)[C:10]([NH:33][CH2:28][C:27]#[N:26])=[O:12])=[CH:6][CH:7]=1

Participants

6

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 11491918Aminoacetonitrile hydrochlorideHCID 22236081HCID 22236081, compound

Product 1

HCID 22236169HCID 22236169, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice cold solution of 2-[(4-bromophenyl)thio]-3-(1-methylcyclopropyl)propanoic acid (417 mg, 1.3 mmol), HATU (652 mg, 1.7 mmol), 2-aminoacetonitrile hydrochloride (171 mg, 1.8 mmol) in DMF (5 mL) was added N,N-diisopropylethylamine (0.68 mL, 3.9 mmol) dropwise. The resulting mixture was stirred at room temperature for 18 h and partitioned between EtOAc and water. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc in hexane to afford 2-[(4-bromophenyl)thio]-N-(cyanomethyl)-3-(1-methylcyclopropyl)propanamide.

Workup

  1. custompartitioned between EtOAc and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-a615fa5032bf429b9cc8da96fa4b4585
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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