Cyanoacetic acid → HCID 24693565, compound

HRID 1961450Notes

Reaction equation

HRID 1961450 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[F:39][C:40]([F:50])([F:49])[C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][CH:48]=1)[CH2:44][NH2:45]>C1COCC1.O>[C:1]([CH2:3][C:4]([NH:45][CH2:44][C:43]1[CH:46]=[CH:47][CH:48]=[C:41]([C:40]([F:39])([F:49])[F:50])[CH:42]=1)=[O:6])#[N:2]

Participants

8

Reactant 5

HCID 9740Cyanoacetic acidHCID 759623-(Trifluoromethyl)benzylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 24693565HCID 24693565, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cyanoacetic acid (297.0 mg, 3.5 mmol), N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride (1.34 g, 7.0 mmol), 1-hydroxybenzotriazole hydrate (641.0 mg, 4.2 mmol) and DIPEA (1.8 g, 14.0 mmol) and 3-(trifluoromethyl)benzylamine (611.0 mg, 3.5 mmol) were suspended in THF. The mixture was heated to 60° for 18 h. Water was added to the mixture and the product extracted with EtOAc, dried over MgSO4 and concentrated. The crude product was purified by flash chromatography, CH2Cl2/MeOH 98:2, yielding 430.0 mg (51%) of the title compound.

Workup

  1. temperatureThe mixture was heated to 60° for 18 h
  2. extractionthe product extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography, CH2Cl2/MeOH 98:2

Sources & evidence

ORD record
ord-bd5c82ef080a44eea61236908d39738d
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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