Hydrochloric Acid → HCID 71735144, compound

HRID 1481103Notes

Reaction equation

HRID 1481103 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].[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][C:35]([NH2:42])([CH2:38][C:39]([OH:41])=[O:40])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C[O-].[Na+].Cl>O.CC(N(C)C)=O>[C:25]([O:29][C:30]([N:32]1[CH2:33][CH2:34][C:35]([CH2:38][C:39]([OH:41])=[O:40])([NH:42][C:3]([C:5]2[N:6]=[C:7]([C:23]#[N:24])[C:8]3[C:13]([C:14]=2[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=3)=[O:4])[CH2:36][CH2:37]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 49759554[4-Amino-1-(tert-butoxycarbonyl)piperidin-4-yl]acetic acidHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 71735144HCID 71735144, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A 20-mL scintillation vial was charged with 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.31 mmol), 4-amino-4-carboxymethyl-piperidine-1-carboxylic acid tert-butyl ester (322 mg, 1.25 mmol), NaOMe (59 mg, 1.09 mmol) and dimethylacetamide (3 mL). It was close-capped and heated in a 150° C. oil bath for 4 h. Reaction mixture was diluted with water (70 mL) and acidified by 1 N HCl to pH=4-5. Precipitate was collected, rinsed with water and dried. Crude product was purified by silica gel chromatography, eluting with 10-100% EtOAc/hexanes, to provide the title compound 92 mg (0.16 mmol) in 54% yield. LC-MS ESI−: 545.08 (M−1)−.

Workup

  1. customIt was close-capped
  2. customReaction mixture
  3. customPrecipitate was collected
  4. washrinsed with water
  5. customdried
  6. customCrude product was purified by silica gel chromatography
  7. washeluting with 10-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-ada17a292a2645bbaafc7fbbcffc14f3
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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