Water → HCID 66616567, compound

HRID 1889659Notes

Reaction equation

HRID 1889659 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1.CCN=C=NCCC[N:27]([CH3:29])C.Cl.[C:31](C(N)C1C=C(C=CC=1)C(O)=O)([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].[CH:49]1[CH:50]=[CH:51][C:52]2N(O)N=N[C:53]=2[CH:54]=1.O.CN([CH:63]=[O:64])C>C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[CH2:5][N:6]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=1)[C:63]([C:49]1[CH:54]=[C:53]([CH:52]=[CH:51][CH:50]=1)[CH2:29][NH:27][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:64]

Participants

9

Reactant 6

HCID 962WaterHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22997357HCID 22997357, compoundHCID 58531427N-(3,5-Dichlorobenzyl)-1-(4-fluorophenyl)methanamine

Product 1

HCID 66616567HCID 66616567, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(3,5-dichlorobenzyl)-1-(4-fluorophenyl)methanamine (0.5 g, 1.76 mmol), EDCI.HCl (0.47 g, 2.46 mmol), 3-(Boc-aminomethyl)benzoic acid (0.53 g, 2.11 mmol) and HOBT.H2O (0.16 g, 1.06 mmol) in DMF (8 mL) was stirred at rt for 20 h. The residue was diluted with ethyl acetate and 1 N HCl solution. The organic layer was separated, washed with 1N NaOH solution, brine, dried over MgSO4, concentrated and the residue was purified by flash chromatography on silica gel (Eluent: A: CH2Cl2, B: ethyl acetate; condition: 100% A to 15% B. (35 min gradient) to obtain the desired product as a white solid (0.81 g, 89%). 1H NMR (CDCl3): δ 7.42-7.32 (m, 5H), 7.17-6.99 (m, 6H), 4.88-4.63 (m, 2H), 4.42-4.35 (m, 4H), 1.47 (s, 9H).

Workup

  1. customThe organic layer was separated
  2. washwashed with 1N NaOH solution, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customthe residue was purified by flash chromatography on silica gel (Eluent

Sources & evidence

ORD record
ord-7717becd6fd242e89edecdb2930caac1
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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