Hydrochloric Acid → HCID 89813075, compound

HRID 1481064Notes

Reaction equation

HRID 1481064 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].Cl.[NH2:26][CH2:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].C[O-].[Na+].CO.Cl>O>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:26][CH2:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30])=[O:4])[N:6]=1)#[N:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 23694274Sodium methanolate methanolHCID 509988433-Amino-2,2-difluoropropanoic acid--hydrogen chloride (1/1)HCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89813075HCID 89813075, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (75 mg, 0.234 mmol) and 3-Amino-2,2-difluoro-propionic acid hydrochloride (122 mg, 0.75 mmol) were placed in a CEM 10 mL Microwave vessel and sodium methoxide-methanol solution (0.5M; 3 mL, 1.5 mmol) was added via syringe. The vessel was sealed and heated to 130° C. in a CEM microwave apparatus for 150 minutes. The reaction mixture was diluted with water and treated with 1N hydrochloric acid and extracted three times with ethyl acetate then dried over sodium sulfate. The solvent was removed in vacuo to provide the title compound as an orange solid in 51% yield. MS ESI(−) m/e: 412.1027 (M−1).

Workup

  1. additionwas added via syringe
  2. customThe vessel was sealed
  3. extractionextracted three times with ethyl acetate
  4. dry with materialthen dried over sodium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8e922ca36e654de786a4a363f027da9f
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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