Hydrochloric Acid → HCID 66802938, compound

HRID 341491Notes

Reaction equation

HRID 341491 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:9][C:10]1[N:15]=[C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[N:13]=[C:12]([C:24](=[NH:27])[NH:25]O)[N:11]=1.C1(C)C=CC=CC=1.Cl>N1C=CC=CC=1.C(Cl)Cl>[NH2:9][C:10]1[N:15]=[C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[N:13]=[C:12]([C:24]2[N:27]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[O:8][N:25]=2)[N:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 20884Ethoxalyl chlorideHCID 178513406HCID 178513406, compound

Product 1

HCID 66802938HCID 66802938, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (0.12 g, 0.84 mmol) was added to a mixture of (4-amino-6-[(3-fluorophenyl)amino]-N-hydroxy-1,3,5-triazine-2-carboximidamide (prepared in an analogous manner to Intermediate 97, 0.20 g, 0.76 mmol) in pyridine (0.12 mL) and toluene (4 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 h and at 110 C for 3 h. The mixture was then cooled at room temperature; DCM (20 mL) and 1M aq. HCl (50 mL) were added. The phases were separated and the aqueous phase was extracted with DCM (2×20 mL). The organic extracts were combined, dried over sodium sulfate, and concentrated. The crude residue was washed with diethyl ether. The organic filtrate was concentrated and purified by flash chromatography to afford the title compound as a yellow solid (45 mg, 17%). Method D HPLC-MS: MH+ requires m/z=346 Found: m/z=346, Rt=2.70 min (40%).

Workup

  1. customat room temperature
  2. temperatureThe mixture was then cooled at room temperature
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with DCM (2×20 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. washThe crude residue was washed with diethyl ether
  8. concentrationThe organic filtrate was concentrated
  9. custompurified by flash chromatography

Sources & evidence

ORD record
ord-031ecd77ca64403eb396e0c0f28e8b7b
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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