Ammonia → HCID 59442088, compound

HRID 1014168Notes

Reaction equation

HRID 1014168 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([F:12])[C:3]=1[C:4](O)=[O:5].CC[N:15]=C=NCCCN(C)C.Cl.Cl.C1C=CC2N(O)N=NC=2C=1.N>O1CCCC1>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([F:12])[C:3]=1[C:4]([NH2:15])=[O:5]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 196120346-Amino-2,3-difluorobenzoic acid

Product 1

HCID 59442088HCID 59442088, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5,6-difluoro benzoic acid (3.78 g, 21.8 mmol) in tetrahydrofuran (500 mL) was added EDCl.HCl (8.5 g, 44.0 mmol, 2.0 equiv.), HOBT (5.9 g, 44 mmol, 2.0 equiv.) and ammonia as a 0.5M solution in dioxanes (218 mL, 109 mmol, 5 equiv.). The resultant slurry was stirred for 24 hours, and then solids removed by filtration through celite. The filtrate was taken to a residue under reduced pressure and partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by chromatography on SiO2 (Ethyl acetate/Hexanes) to afford analytically pure 2-amino-5,6-difluorobenzamide as a white crystalline solid (2.73 g, 15.8 mmol, 72% Yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.78 (s, 2 H), 6.45 (ddd, J=9.16, 4.03, 1.83 Hz, 1 H), 7.10-7.18 (m, 1 H), 7.69 (d, J=11.00 Hz, 2 H).

Workup

  1. customsolids removed by filtration through celite
  2. custompartitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. custompurified by chromatography on SiO2 (Ethyl acetate/Hexanes)

Sources & evidence

ORD record
ord-0cfe5f2d06c04b6ea5ca1c962cce5874
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…