Triethylamine → HCID 178473505, compound

HRID 724318Notes

Reaction equation

HRID 724318 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.[CH2:35]([O:37][C:38](Cl)=[O:39])[CH3:36]>ClCCl>[CH2:35]([O:37][C:38](=[O:39])[NH:2][C@H:3]1[CH2:8][CH2:7][C@@H:6]([NH:9][C:10]([C:11]2[C:12]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH3:26])[CH:20]=3)=[N:13][CH:14]=[C:15]([F:17])[CH:16]=2)=[O:27])[CH2:5][CH2:4]1)[CH3:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178503208HCID 178503208, compound

Product 1

HCID 178473505HCID 178473505, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(cis-4-Amino-cyclohexyl)-5-fluoro-2-(3-methylsulfanyl-phenoxy)-nicotinamide hydrochloride (150 mg, 0.364 mmol) was suspended in dichloromethane (2 ml) under nitrogen at room temperature and triethylamine (153 μl, 1.09 mmol) was added followed by ethylchloroformate (39 μl, 0.4 mmol). The reaction was stirred at room temperature for 1.5 h and the mixture was quenched with sat. sodium bicarbonate solution (3 ml). The organic phase was separated and the aqueous phase was washed with dichloromethane (2×3 ml). The combined organic extracts were dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (98:2, by volume) and the product was triturated with diethylether (3 ml) to give (cis-4-{[5-Fluoro-2-(3-methylsulfanyl-phenoxy)-pyridine-3-carbonyl]-amino}-cyclohexyl)-carbamic acid ethyl ester (64 mg) as a white solid.

Workup

  1. customthe mixture was quenched with sat. sodium bicarbonate solution (3 ml)
  2. customThe organic phase was separated
  3. washthe aqueous phase was washed with dichloromethane (2×3 ml)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (98:2, by volume)
  7. customthe product was triturated with diethylether (3 ml)

Sources & evidence

ORD record
ord-96537150cac84fe4951fe4b2ab2c5172
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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