Sodium Methoxide → HCID 178510583, compound

HRID 1481095Notes

Reaction equation

HRID 1481095 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@H:26]1[CH2:31][CH2:30][C@H:29]([C:32]([OH:34])=[O:33])[CH2:28][CH2:27]1.C[O-].[Na+]>COCCO>[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@H:26]2[CH2:31][CH2:30][C@H:29]([C:32]([OH:34])=[O:33])[CH2:28][CH2:27]2)=[O:4])[N:6]=1)#[N:24]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylateHCID 178511567HCID 178511567, compound

Product 1

HCID 178510583HCID 178510583, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

To a mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (60 mg, 0.19 mmol) and trans-4-amino-cyclohexanecarboxylic acid (107 mg, 0.75 mmol) in 3 mL of 2-methoxyethanol was added NaOMe solid (30 mg, 0.56 mmol). The resultant mixture was microwaved at 140° C. for 1 h. Reaction mixture was concentrated and residue was dissolved in water (60 mL). It was acidified by 1 N HCl to pH=3-4. Precipitate was collected, and rinsed with water and MeOH. Solid was dried to provide the title compound 40 mg (0.093 mmol) in 49% yield. LC-MS ESI−: 430.00 (M−1)−.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. dissolutionresidue was dissolved in water (60 mL)
  4. customPrecipitate was collected
  5. washrinsed with water and MeOH
  6. customSolid was dried

Sources & evidence

ORD record
ord-813a0d0d14a74a1793370e0f7a3cecb8
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…