1,2-Dichloroethane → HCID 59730339, compound

HRID 492644Notes

Reaction equation

HRID 492644 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:14][C:15]1[CH:30]=[CH:29][C:18]([O:19][C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][N:21]=2)=[CH:17][CH:16]=1)[CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=[N:41][C:39]=2C=1.CCN(C(C)C)C(C)C.Cl.CN.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][CH:11]([CH3:12])[CH3:13])[CH2:14][C:15]1[CH:30]=[CH:29][C:18]([O:19][C:20]2[CH:28]=[CH:27][C:23]([C:24](=[O:26])[NH:41][CH3:39])=[CH:22][N:21]=2)=[CH:17][CH:16]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

9

Reactant 7

HCID 111,2-DichloroethaneHCID 311Citric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 6364545Methylamine hydrochlorideHCID 59730271HCID 59730271, compound

Product 1

HCID 59730339HCID 59730339, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 6-(4-{[tert-Butoxycarbonyl-(3-methyl-butyl)-amino]-methyl}-phenoxy)-nicotinic acid (0.090 g, 0.21 mmol), CH2Cl2 (5 mL), EDC (0.048 g, 0.25 mmol), HOBt (0.034 g, 0.25 mmol), Hunig's Base (92 uL, 0.53 mmol), and Methylamine Hydrochloride (0.014 g, 0.21 mmol) in a 7 mL reaction vial. After reactions shake for 72 hours, add 10% Citric acid, followed by 10% NaHCO3, and then add the organic mixture to a Celite column. Elute with CH2Cl2, concentrate, and flash chromatograph using 2:1 Ethyl acetate:Hexanes eluent to afford 56.2 mg (63% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 0.9 (6H, d), 1.3-1.6 (12H, m), 3.0 (3H, s), 3.1-3.3 (2H, m), 4.3-4.5 (2H, m), 6.3 (1H, br s), 6.9 (1H, d), 7.1 (2H, d), 7.2-7.4 (2H, m), 8.1 (1H, d), 8.5 (1H, s); MS m/z 328 (M−100, Boc).

Workup

  1. additionadd the organic mixture to a Celite column
  2. washElute with CH2Cl2
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-e588f2c1d9e24b9989c0c65dd07be959
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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