Ethylamine hydrochloride → HCID 67497734, compound

HRID 1628345Notes

Reaction equation

HRID 1628345 reaction equation
Cl.[CH2:2]([NH2:4])[CH3:3].C[Al](C)C.[CH3:9][N:10]1[C:14]([NH:15][C:16](=[O:32])[C@@H:17]([NH:25][CH2:26][C:27](OCC)=[O:28])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][C:12]([C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)=[N:11]1.[Cl-].[NH4+]>ClCCl>[CH2:2]([NH:4][C:27]([CH2:26][NH:25][C@@H:17]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16]([NH:15][C:14]1[N:10]([CH3:9])[N:11]=[C:12]([C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)[CH:13]=1)=[O:32])=[O:28])[CH3:3]

Participants

6

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 67497930HCID 67497930, compound

Product 1

HCID 67497734HCID 67497734, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 25 ml flask was added ethylamine hydrochloride (245 mg, 3.00 mmole) and 7 ml of dichloromethane. Trimethylaluminum (1.0M in hexane, 6.0 ml, 6.0 mmole) was added to the solution at room temperature. After 10 min, a solution of ethyl 2-((S)-1-(1-methyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylamino)acetate 17.7 (408 mg, 1.00 mmole) in 3 ml of dichloromethane was added to the reaction mixture. The reaction was stirred at room temperature overnight. After then, the solution was poured into saturated ammonium chloride, and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. After concentration in vacuo, the residue was chromatographed on silica gel to give 104.2 (283 mg, 70% yield) as colorless amorphous. LCMS ESI (pos.) m/e: 407 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 9.76 (s, 1H), 8.61 (d, J=6.3 Hz, 2H), 7.66 (d, J=6.2 Hz, 2H), 7.38-7.29 (m, 5H), 6.82 (s, 1H), 5.80 (brs, 1H), 3.79 (s, 3H), 3.49 (brs, 1H), 3.29-3.20 (m, 5H), 2.93 (dd, J=13.6, 8.9 Hz, 1H), 2.14 (brs, 1H), 1.07 (t, J=7.2 Hz, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationAfter concentration in vacuo
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-87f0cbfdfde64f62a93f83498d8af5e7
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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