Triethylamine → HCID 178503200, compound

HRID 724338Notes

Reaction equation

HRID 724338 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:26])[C:11]2[CH:16]=[CH:15][CH:14]=[N:13][C:12]=2[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([S:24][CH3:25])[CH:19]=2)[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH:34]1([CH2:37][C:38](O)=[O:39])[CH2:36][CH2:35]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[CH:34]1([CH2:37][C:38]([NH:2][C@@H:3]2[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:26])[C:11]3[CH:16]=[CH:15][CH:14]=[N:13][C:12]=3[O:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24][CH3:25])[CH:19]=3)[CH2:5][CH2:4]2)=[O:39])[CH2:36][CH2:35]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 138440Cyclopropaneacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178503199HCID 178503199, compound

Product 1

HCID 178503200HCID 178503200, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(cis-4-Aminocyclohexyl)-2-[3-(methylsulfanyl)phenoxy]nicotinamide hydrochloride (100 mg, 0.25 mmol) was dissolved in dimethylformamide (1.7 ml) and triethylamine (106 μl, 0.76 mmol) was added followed by cyclopropylacetic acid (28 mg, 0.25 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (97 mg, 0.51 mmol) and 1-hydroxybenzotriazole (38 mg, 0.28 mmol). The reaction was stirred under nitrogen at room temperature for 18 h and the solvent was removed under reduced pressure. The residue was suspended in saturated aqueous sodium bicarbonate solution (5 ml) and extracted with ethyl acetate (3×10 ml). The organic phase was washed with brine (5 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was triturated with diethyl ether to give N-{cis-4-[(cyclopropylacetyl)amino]cyclohexyl}-2-[3-(methylsulfanyl)phenoxy]nicotinamide (99 mg) as a white solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. extractionextracted with ethyl acetate (3×10 ml)
  3. washThe organic phase was washed with brine (5 ml)
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-f07e934f2f204643b39e17762ada3d34
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

Loading…