Triethylamine → HCID 178503223, compound

HRID 724335Notes

Reaction equation

HRID 724335 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:27])[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[N:13][C:12]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH3:26])[CH:20]=2)[CH2:5][CH2:4]1.C(N(CC)CC)C.[Cl:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40](Cl)=[O:41]>ClCCl>[Cl:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:27])[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[N:13][C:12]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH3:26])[CH:20]=2)[CH2:5][CH2:4]1)=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 740895-Chlorovaleryl chlorideHCID 178503209HCID 178503209, compound

Product 1

HCID 178503223HCID 178503223, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(trans-4-Amino-cyclohexyl)-5-fluoro-2-(3-methylsulfanyl-phenoxy)-nicotinamide hydrochloride (400 mg, 1.065 mmol) was dissolved in dichloromethane (6 ml) and triethylamine (445 μl, 3.20 mmol) was added followed by dropwise addition of 5-chlorovaleryl chloride (151 μl, 1.172 mmol). The reaction was stirred under nitrogen at room temperature for 4 h. The reaction mixture was quenched with sat. sodium hydrogen carbonate solution (10 ml) and extracted with dichloromethane (3×15 ml). The combined organic extracts were dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by column chromatography, eluting with 95:5 dichloromethane/methanol, clean fractions were combined and the solvent was removed under reduced pressure to obtain the title compound (220 mg) as a white solid.

Workup

  1. customThe reaction mixture was quenched with sat. sodium hydrogen carbonate solution (10 ml)
  2. extractionextracted with dichloromethane (3×15 ml)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography
  6. washeluting with 95:5 dichloromethane/methanol, clean fractions
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bf4fd331c25741e3b235074158606e1c
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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