Hydrochloric Acid → HCID 178513111, compound

HRID 2171725Notes

Reaction equation

HRID 2171725 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 1M 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. 1M 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-08695babd4a4417c810ddbb2391741e3
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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