Hydrochloric Acid → HCID 178513111, compound

HRID 1021324Notes

Reaction equation

HRID 1021324 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][C:27](=[O:32])[NH:28][C:29](=[NH:31])[NH2:30])[C:20]=3[F:33])[CH2:15][CH2:14]2)=[CH:9][N:8]=1)=[O:6].C1COCC1.Cl>CO>[C:29]([NH:28][C:27]([O:26][CH2:25][C:21]1[C:20]([F:33])=[C:19]([N:16]2[CH2:17][CH2:18][N:13]([C:10]3[CH:11]=[CH:12][C:7]([C:5]([OH:6])=[O:4])=[N:8][CH:9]=3)[CH2:14][CH2:15]2)[CH:24]=[CH:23][CH:22]=1)=[O:32])(=[NH:30])[NH2:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 178498102HCID 178498102, compound

Product 1

HCID 178513111HCID 178513111, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 M aqueous NaOH solution (1.14 ml) was added to a mixture of 5-[4-(3-{[(carbamimidoylcarbamoyl)oxy]methyl}-2-fluorophenyl)piperazin-1-yl]pyridine-2-carboxylate methyl ester (326 mg), THF (9 ml), and MeOH (3 ml), followed by stirring at room temperature overnight. 1 M hydrochloric acid (1.14 ml) was added to the reaction mixture, followed by stirring at room temperature for 1 hour. The generated solid was collected by filtration, washed with water, and then dried at 50° C. under reduced pressure to obtain 5-[4-(3-{[(carbamimidoylcarbamoyl)oxy]methyl}-2-fluorophenyl)piperazin-1-yl]pyridine-2-carboxylic acid (293 mg).

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. filtrationThe generated solid was collected by filtration
  3. washwashed with water
  4. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-73db75f07cdc4883b04d95d8cf4dd365
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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