Triethylamine → N-(4-(2-tert-Butyl-4-chlorophenoxy)butyl)-4-hydroxy-3-(morpholinomethyl)-benzamide

HRID 1009513Notes

Reaction equation

HRID 1009513 reaction equation
Cl.[C:2]([C:6]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])([CH3:5])([CH3:4])[CH3:3].[OH:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][C:21]=1[CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:2]([C:6]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([OH:19])=[C:21]([CH2:29][N:30]2[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)[CH:22]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 41378034-Hydroxy-3-(morpholin-4-ylmethyl)benzoic acidHCID 574473074-(2-Tert-butyl-4-chloro-phenoxy)-butylamine hydrochloride

Product 1

HCID 57647174N-(4-(2-tert-Butyl-4-chlorophenoxy)butyl)-4-hydroxy-3-(morpholinomethyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2-tert-butyl-4-chloro-phenoxy)-butylamine hydrochloride (0.102 g, 0.35 mmol), 4-hydroxy-3-morpholin-4-ylmethyl-benzoic acid (0.091 g, 0.385 mmol), triethylamine (54 μL, 0.385 mmol), N-hydroxybenzotriazole (0.059 g, 0.385 mmol), EDC HCl (0.074 g, 0.385 mmol) in dry DMF was stirred for 3 h at room temperature. 20 mL of a 5% sodium bicarbonate solution was added, and the reaction was extracted with dichloromethane (3×20 mL). The combined organic layers were washed with 10% hydrochloric acid (1×20 mL), brine (2×20 mL) and dried over sodium sulfate. The solvent was removed in vacuo, the residue was triturated with a mixture of diethyl ether and ethyl acetate. The crude product was purified by flash chromatography (Kieselgel 60H) using chloroform:methanol (10:3) as an eluent. Yield: 0.070 g (42%) 6-1. LCMS: method A, Rt: 1.80 min, M+H=475).

Workup

  1. extractionthe reaction was extracted with dichloromethane (3×20 mL)
  2. washThe combined organic layers were washed with 10% hydrochloric acid (1×20 mL), brine (2×20 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue was triturated with a mixture of diethyl ether and ethyl acetate
  6. customThe crude product was purified by flash chromatography (Kieselgel 60H)

Sources & evidence

ORD record
ord-eef463e26fac4bf19d585dfd469178fd
Source dataset
uspto-grants-2011_07
Patent number
US07973079B2

Reaction notes

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