Triethylamine → HCID 69586633, compound

HRID 724311Notes

Reaction equation

HRID 724311 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH3:19])[CH:13]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(N(CC)CC)C.Cl.[OH:28][CH2:29][C@H:30]1[CH2:35][CH2:34][CH2:33][CH2:32][C@H:31]1[NH2:36].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[F:1][C:2]1[CH:3]=[N:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH3:19])[CH:13]=2)=[C:6]([CH:10]=1)[C:7]([NH:36][C@@H:31]1[CH2:32][CH2:33][CH2:34][CH2:35][C@@H:30]1[CH2:29][OH:28])=[O:9]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 113918232-[3-(Methylsulfanyl)phenoxy]-5-fluoronicotinic acidHCID 23545866HCID 23545866, compound

Product 1

HCID 69586633HCID 69586633, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Fluoro-2-(3-methylsulfanyl-phenoxy)-nicotinic acid (200 mg, 0.716 mmol) was dissolved in dimethylformamide (3 ml) and triethylamine (300 μl, 2.14 mmol) was added followed by cis-2-hydroxymethyl-1-cyclohexylamine hydrochloride (125 mg, 0.755 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (151 mg, 0.788 mmol) and 1-hydroxybenzotriazole(106 mg, 0.785 mmol). The reaction was stirred at room temperature for 18 h and the solvent was removed under reduced pressure. The residue was partitioned between water (30 ml) and ethyl acetate (30 ml). The organic phase dried over Na2SO4, the solvent removed under reduced pressure, and the residue purified by column chromatography on silica gel using dichloromethane:methanol (95:5) as eluent to afford an oil which crystallized from n-pentane to give the title compound as a white solid (136 mg).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between water (30 ml) and ethyl acetate (30 ml)
  3. dry with materialThe organic phase dried over Na2SO4
  4. customthe solvent removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel
  6. customto afford an oil which
  7. customcrystallized from n-pentane

Sources & evidence

ORD record
ord-f824f51f4f0342e8a5526dd4ff7d50c9
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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