Hydrochloric Acid → HCID 89813162, compound

HRID 1481114Notes

Reaction equation

HRID 1481114 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].[NH2:25][C:26]1([CH2:30][C:31]([OH:33])=[O:32])[CH2:29][CH2:28][CH2:27]1.C[O-].[Na+].Cl>CC(N(C)C)=O.O>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:25][C:26]2([CH2:30][C:31]([OH:33])=[O:32])[CH2:29][CH2:28][CH2:27]2)=[O:4])[N:6]=1)#[N:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 21504672HCID 21504672, compoundHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89813162HCID 89813162, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (45 mg, 0.14 mmol) and (1-amino-cyclobutyl)-acetic acid (91 mg, 0.70 mmol) (APAC Pharmaceuticals LLC, Columbia Md.) in DMA (2 mL) was added NaOMe solid (38 mg, 0.70 mmol). The resultant mixture was heated in a 150° C. oil bath for 3 h. Reaction mixture was diluted with water and acidified by 1 N HCl to pH=3-4. Precipitate was collected, rinsed with water and dried in vacuo to provide the title compound 54 mg (0.13 mmol) in 92% yield. LC-MS ESI−: 416.17 (M−1)−.

Workup

  1. customReaction mixture
  2. customPrecipitate was collected
  3. washrinsed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-867cb63cbaee498ba7315640c75c1234
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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