1,2-Dichloroethane → HCID 59730317, compound

HRID 228471Notes

Reaction equation

HRID 228471 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:17][C:18]1[CH:33]=[CH:32][C:21]([O:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][N:24]=2)=[CH:20][CH:19]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=C[C:41]2N(O)N=[N:44][C:42]=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]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:22][C:23]2[CH:31]=[CH:30][C:26]([C:27](=[O:29])[NH:44][CH2:42][CH3:41])=[CH:25][N:24]=2)=[CH:32][CH:33]=1)[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

9

Reactant 7

HCID 111,2-DichloroethaneHCID 311Citric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 6364545Methylamine hydrochlorideHCID 59730322HCID 59730322, compound

Product 1

HCID 59730317HCID 59730317, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 6-{4-[(tert-Butoxycarbonyl-phenethyl-amino)-methyl]-phenoxy}-nicotinic acid (0.097 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 55.4 mg (57% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 1.4 (9H, s), 2.7-2.9 (21 m), 3.0 (3H, s), 4.2-4.4 (2H, m), 4.3-4.5 (2H, m), 6.3-6.4 (1H, br s), 6.9 (1H, d), 7.0-7.4 (9H, m), 8.1 (1H, d), 8.6 (1H, s); MS m/z 362 (M−100, Boc).

Workup

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

Sources & evidence

ORD record
ord-bdb7f2c25c0e4875925c507b9f05f343
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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