Triethylamine → HCID 178496463, compound

HRID 724290Notes

Reaction equation

HRID 724290 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[N:12][C:11]=2[Cl:17])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:26][O:27][CH2:28][C:29](O)=[O:30].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:17][C:11]1[N:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=1[C:9]([NH:8][C@H:5]1[CH2:6][CH2:7][C@@H:2]([NH:1][C:29](=[O:30])[CH2:28][O:27][CH3:26])[CH2:3][CH2:4]1)=[O:18]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 12251Methoxyacetic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178511677HCID 178511677, compound

Product 1

HCID 178496463HCID 178496463, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(cis-4-Aminocyclohexyl)-2-chloro-5-fluoronicotinamide (837 mg, 2.72 mmol) and triethylamine (1.14 ml, 8.15 mmol) were dissolved in dimethylformamide (20 ml) and 2-methoxy acetic acid (208 μl, 2.72 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (573 mg, 2.99 mmol) and 1-hydroxybenzotriazole (404 mg, 2.99 mmol) were added. The reaction was stirred under nitrogen at room temperature for 18 h then partitioned between water and ethyl acetate. The organic phase was dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting using dichloromethane:methanol (96:4 to 91:9) as eluant to give 2-chloro-5-fluoro-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}nicotinamide (550 mg).

Workup

  1. customthen partitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel eluting

Sources & evidence

ORD record
ord-cd707be76ba54c70b01791cd8b48c01f
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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