Picolinic acid → HCID 178503215, compound

HRID 724340Notes

Reaction equation

HRID 724340 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.[N:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41](O)=[O:42].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[F:17][C:15]1[CH:16]=[C:11]([C:10]([NH:9][C@H:6]2[CH2:7][CH2:8][C@H:3]([NH:2][C:41]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][N:35]=3)=[O:42])[CH2:4][CH2:5]2)=[O:27])[C:12]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH3:26])[CH:20]=2)=[N:13][CH:14]=1

Participants

7

Reactant 5

HCID 1018Picolinic acidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178503209HCID 178503209, compound

Product 1

HCID 178503215HCID 178503215, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(trans-4-amino-cyclohexyl)-5-fluoro-2-(3-methylsulfanyl-phenoxy)-nicotinamide hydrochloride (250 mg, 0.666 mmol) in dimethylformamide (5 ml) and triethylamine (278 μl, 2.0 mmol) was treated with 2-pyridine carboxylic acid (90 mg, 0.73 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (141 mg, 0.73 mmol) and 1-hydroxybenzotriazole (99 mg, 0.73 mmol). The reaction was stirred under nitrogen at room temperature for 18 h and the solvent was removed under reduced pressure. The residue was partitioned between sat. sodium hydrogen carbonate solution (10 ml) and ethyl acetate (15 ml) and the aqueous phase was extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with water (2×10 ml), brine (10 ml), dried over MgSO4 and the solvent was removed under reduced pressure to give the title compound (175 mg) as a white solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between sat. sodium hydrogen carbonate solution (10 ml) and ethyl acetate (15 ml)
  3. extractionthe aqueous phase was extracted with ethyl acetate (3×15 ml)
  4. washThe combined organic extracts were washed with water (2×10 ml), brine (10 ml)
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2283eaaafc5745e8a6e96cf8de7fd1a0
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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