Triethylamine → HCID 69065113, compound

HRID 1436875Notes

Reaction equation

HRID 1436875 reaction equation
[C:1]([C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH2:8][CH:9]=[CH2:10])[CH2:4][C:5]([OH:7])=O)#[N:2].[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C=O)C>[C:1]([C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH2:8][CH:9]=[CH2:10])[CH2:4][C:5]([NH:23][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=1)=[O:7])#[N:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69060272HCID 69060272, compound

Product 1

HCID 69065113HCID 69065113, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution f 3-cyano-3-phenylhex-5-enoic acid (5.66 g, 26.3 mmol) and 4-fluorobenzylamine (3.95 g, 31.6 mmol) in DMF was added 1-hydroxybenzotriazole hydrate (6.04 g, 39.4 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (7.56 g, 39.4 mmol), and triethylamine (3.19 g, 31.5 mmol). After stirring overnight at room temperature, the reaction mixture was concentrated under vacuum. The residue was partitioned between EtOAc and water. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum to provide the title compound as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.41 (s, 1H), 7.47 (d, J=7.9 Hz, 2H), 7.36 (t, J=7 Hz, 2H) 7.35 (t, J=7 Hz, 1H), 7.04 (t, J=8.9 Hz, 2H), 6.97 (t, J=8.6 Hz, 2H), 5.53 (m, 1H), 5.12 (m, 2H), 4.21 (m, 1H), 4.08 (m, 1H), 2.88 (m, 3H), 2.77 (m, 1H) ppm. ES MS M+1=323.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. customThe residue was partitioned between EtOAc and water
  3. extractionThe organic extract
  4. dry with materialwas dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ebb09686c603486aa92b379646d3f2d9
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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