Hydrochloric Acid → HCID 59415964, compound

HRID 2061880Notes

Reaction equation

HRID 2061880 reaction equation
C[N:2]([CH3:20])/[CH:3]=[C:4](/[C:10](=[O:19])[C:11]1[CH:16]=[C:15]([I:17])[CH:14]=[CH:13][C:12]=1F)\[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl.[CH3:22][N:23]([CH3:28])[CH:24](C)[CH2:25]N.C(=O)([O-])[O-].[K+].[K+].Cl>C1COCC1.CN(C=O)C>[CH3:22][N:23]([CH3:28])[CH:24]([CH3:25])[CH2:20][N:2]1[C:12]2[C:11](=[CH:16][C:15]([I:17])=[CH:14][CH:13]=2)[C:10](=[O:19])[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium Carbonate2×HCID 429336831177335-06-6HCID 70809441(Z)-ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate2×

Product 1

HCID 59415964HCID 59415964, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

(Z)-Ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate (0.500 g, 1.28 mmol, Intermediate 24), N2,N2-dimethylpropane-1,2-diamine hydrochloride (0.177 g, 1.28 mmol), and potassium carbonate (0.194 g, 1.41 mmol) were combined in THF (10.0 mL). The reaction was heated at 60° C. for 2 hrs. After 2 h, DMF (5.0 mL) was added followed by potassium carbonate (0.530 g, 3.83 mmol). The reaction was heated at 90° C. for 6 h. The reaction mixture was cooled to 0° C. and 1N HCl was slowly added until pH was around 4. The resulting precipitate was filtered, washed with water and dried overnight to yield a light yellow solid (0.428 g).

Workup

  1. temperatureThe reaction was heated at 90° C. for 6 h
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried overnight

Sources & evidence

ORD record
ord-44d412234bf94250ab1019084da174b1
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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