Triethylamine → HCID 59153166, compound

HRID 2355295Notes

Reaction equation

HRID 2355295 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]=[CH:3]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.Cl.[NH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][OH:43])=[CH:38][CH:37]=1.C(N(CC)CC)C>C(#N)C>[OH:43][CH2:42][C:39]1[CH:40]=[CH:41][C:36]([CH2:35][NH:34][C:7]([C:5]2[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=2)=[O:9])=[CH:37][CH:38]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 46738133[4-(Aminomethyl)phenyl]methanol--hydrogen chloride (1/1)

Product 1

HCID 59153166HCID 59153166, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Stir a mixture of 1-methyl-1H-imidazole-4-carboxylic acid (4.0 g, 31.67 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6.6 g, 34.5 mmol) and 1-hydroxybenzotriazole hydrate (5.29 g, 34.5 mmoles) in anhydrous acetonitrile (150 mL) at room temperature for 1 hr. Add to the reaction mixture (4-aminomethyl-phenyl)-methanol hydrochloride (5.0 g, 28.8 mmol) and triethylamine (8.4 mL, 60.5 mmol). Stir the reaction mixture at room temperature overnight. Quench the reaction mixture with water and extract with ethyl acetate (3×). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate to provide the title compound (4.6 g, 18.8 mmol). MS (m/z): 246 (M+1).

Workup

  1. stirringStir the reaction mixture at room temperature overnight
  2. customQuench the reaction mixture with water
  3. extractionextract with ethyl acetate (3×)
  4. washCombine the organic layers, wash with brine
  5. dry with materialdry over sodium sulfate
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-55368f18428e40f697f4493b7f12df8b
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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