Hydrochloric Acid → HCID 71737070, compound

HRID 1481092Notes

Reaction equation

HRID 1481092 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][CH2:26][CH:27]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:28]([OH:30])=[O:29].C[O-].[Na+].CO.Cl>O>[C:35]([O:34][C:32]([NH:31][C@@H:27]([CH2:26][NH:25][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:28]([OH:30])=[O:29])=[O:33])([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 32971953-Amino-2-{[(tert-butoxy)carbonyl]amino}propanoic acidHCID 23694274Sodium methanolate methanolHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 71737070HCID 71737070, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °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), 3-amino-2-tert-butoxycarbonylamino-propionic acid (319 mg, 1.56 mmol) (Bachem) and 0.5 M NaOMe/MeOH solution (2.5 mL, 1.25 mmol). The vial was close capped and heated in a 90-100° C. oil bath for 2 days. Reaction mixture was diluted with water (70 mL), acidified by 1 N HCl to pH=3-4. Precipitate was collected, rinsed with water and dried in vacuo to provide the title compound 108 mg (0.22 mmol) in 71% yield. LC-MS ESI−: 491.16 (M−1)−.

Workup

  1. customThe vial was close
  2. customcapped
  3. customReaction mixture
  4. customPrecipitate was collected
  5. washrinsed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-56c68ab4162240cebc3be358c020bb4d
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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