Hydrochloric Acid → HCID 68440365, compound

HRID 505451Notes

Reaction equation

HRID 505451 reaction equation
C[O:2][C:3]([CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[NH:17][C:18]([NH:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[Cl:29])=[O:19])[C:10]([O:12]C)=[O:11])=[O:4].O.[Li+].[OH-].Cl>C1COCC1>[C:3]([CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[NH:17][C:18]([NH:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[Cl:29])=[O:19])[C:10]([OH:12])=[O:11])([OH:4])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 69887611HCID 69887611, compound

Product 1

HCID 68440365HCID 68440365, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude product from step a) is converted in analogy to examples 1b) to 1d) into methyl 3-methoxycarbonylrnethoxy-4-[3-(2-chloro-4-fluorobenzoyl)ureido]-benzoate, of which 50 mg (0.11 mmol) are dissolved in 5 ml of THF, and 1 ml of water is added. To this are added 27 mg (1.1 mmol) of LiOH, and the reaction is stirred at room temperature until the precursor has reacted completely. The reaction is monitored by LC-MS. After completion of the reaction, the mixture is acidified with dilute hydrochloric acid and extracted twice with 20 ml of ethyl acetate each time. The combined organic phases are dried over Na2SO4, filtered and concentrated in a rotary evaporator, and the residue obtained in this way is purified in a preparative HPLC system (column: Waters Xterra™ MS C18, 5 μm, 30×100 mm, mobile phases: A: H2O+0.2% trifluoroacetic acid, B: acetonitrile, gradient: 2.5 minutes 90% A/10% B to 17.5 minutes 10% A/90% B). 28 mg (0.068 mmol) of the desired product are obtained.

Workup

  1. customhas reacted completely
  2. customAfter completion of the reaction
  3. extractionextracted twice with 20 ml of ethyl acetate each time
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in a rotary evaporator
  7. customthe residue obtained in this way
  8. customis purified in a preparative HPLC system (column

Sources & evidence

ORD record
ord-dd00ab7fe2544c9e9fef5e7afff3c06d
Source dataset
uspto-grants-2010_08
Patent number
US07781459B2

Reaction notes

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