Triethylamine → N-(2-amino-4-fluorophenyl)-6-chloronicotinamide

HRID 1695038Notes

Reaction equation

HRID 1695038 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.[F:40][C:41]1[CH:46]=[CH:45][C:44]([NH2:47])=[C:43]([NH2:48])[CH:42]=1>[Cl-].[Na+].O.CN(C=O)C>[NH2:48][C:43]1[CH:42]=[C:41]([F:40])[CH:46]=[CH:45][C:44]=1[NH:47][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[N:3][CH:4]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 1645844-Fluorobenzene-1,2-diamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 57993734N-(2-amino-4-fluorophenyl)-6-chloronicotinamideYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-Chloronicotinic acid (157.5 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and 4-fluoro-o-phenylenediamine (151 mg, 1.2 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine and extracted with 200 ml of ethyl acetate. The ethyl acetate was removed under vacuum. To the residue was added 5 ml of absolute ethanol. The solids were collected by vacuum filtration, washed with absolute ethanol and dried under vacuum to give the title compound (193 mg, 73% yield) as a brown solid. LC-MS (m/z) 266 (M+1).

Workup

  1. additionwere added
  2. extractionextracted with 200 ml of ethyl acetate
  3. customThe ethyl acetate was removed under vacuum
  4. additionTo the residue was added 5 ml of absolute ethanol
  5. filtrationThe solids were collected by vacuum filtration
  6. washwashed with absolute ethanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-208c1e8e0ccb47d3a600621848ce5a38
Source dataset
uspto-grants-2012_04
Patent number
US08158656B2

Reaction notes

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