1-Chloro-2-(diethylamine)ethane hydrochloride → 3-{3-[4-(1-Hydroxy-1-methyl-ethyl)-benzylcarbamoyl]-pyridin-2-yloxy}-benzoicacid methyl ester

HRID 844058Notes

Reaction equation

HRID 844058 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:18]=[CH:19][CH:20]=1)[O:8][C:9]1[N:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)=[O:4].[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([OH:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N(CC)CCCl)C>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:20]=[CH:19][CH:18]=[C:7]([O:8][C:9]2[C:10]([C:11](=[O:13])[NH:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([OH:32])([CH3:30])[CH3:31])=[CH:25][CH:24]=3)=[CH:14][CH:15]=[CH:16][N:17]=2)[CH:6]=1

Participants

7

Reactant 4

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 101542112-[4-(Aminomethyl)phenyl]propan-2-olHCID 226122032-(3-Methoxycarbonyl-phenoxy)-nicotinic acid

Product 1

HCID 226121183-{3-[4-(1-Hydroxy-1-methyl-ethyl)-benzylcarbamoyl]-pyridin-2-yloxy}-benzoicacid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(3-Methoxycarbonyl-phenoxy)-nicotinic acid (0.400 grams, 1.463 mmole), 2-(4-Aminomethyl-phenyl)-propan-2-ol (0.266 grams, 1.61 mmole), and 1-hydroxybenzotriazole hydrate (0.237 grams, 1.755 mmole) in dry dimethylformamide (20 ml) was added 2-diethylaminoethyl chloride hydrochloride (0.365 grams, 1.90 mmole) and stirred over night. The mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to give a white foam. (0.360 g); MS (m/e) 420 (M++1); 1H NMR (CDCl3) d 1.50 (6H, s), 3.90 (3H, s), 4.70 (2H, d, J=5.60 Hz), 7.20-8.65 (12H, m).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a white foam

Sources & evidence

ORD record
ord-5b1dd6131eba451c8ad4347b9d057f3d
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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