Ammonia → HCID 59656711, compound

HRID 2054905Notes

Reaction equation

HRID 2054905 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:19]=[C:18]([F:20])[C:14]([C:15](O)=[O:16])=[C:13]([F:21])[CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([N:24](CC)CC)C.ClC(OCC)=O.N>C1COCC1>[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:19]=[C:18]([F:20])[C:14]([C:15]([NH2:24])=[O:16])=[C:13]([F:21])[CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 59656676HCID 59656676, compound

Product 1

HCID 59656711HCID 59656711, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the above benzoic cid intermediate (1.23 g, 4.08 mmol) and triethylamine (0.63 mL, 4.5 mmol) in THF (20 mL) at −25° C. was added ethyl chloroformate (0.43 mL, 4.5 mmol). The reaction was warmed to 0° C. in 1 h and an ammonia solution (0.5 N in dioxane, 20 mL, 10 mmol) was then added. The reaction was stirred at room temperature overnight, concentrated, diluted with dichloromethane, washed with 1N HCl and brine, dried with sodium sulfate, concentrated, and dried in vacuo to give 4-(N-boc-2-aminoethyl)-2,6-difluorobenzamide (0.8 g, 65%).

Workup

  1. concentrationconcentrated
  2. additiondiluted with dichloromethane
  3. washwashed with 1N HCl and brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3b194eedb8d2493b9dfbd52508a4a16d
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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