5-Aminovaleric acid → HCID 71736744, compound

HRID 1481088Notes

Reaction equation

HRID 1481088 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][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31].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:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:4])[N:6]=1)#[N:24]

Participants

6

Reactant 4

HCID 1385-Aminovaleric acidHCID 313Hydrochloric AcidHCID 23694274Sodium methanolate methanolHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 71736744HCID 71736744, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.31 mmol) and 5-amino-pentanoic acid (110 mg, 0.94 mmol) (Aldrich) in 0.5 M NaOMe/MeOH (1.25 mL, 0.63 mmol) was microwaved at 120° C. for 1 h. Reaction mixture was diluted with water (60 mL), acidified by 1 N HCl to pH=3-4. Precipitate was collected and dried. The crude product was triturated with MeOH (2 mL). Solid was collected and dried in vacuo to provide the title compound 65 mg (0.16 mmol) in 52% yield. LC-MS ESI−: 404.03 (M−1)−.

Workup

  1. customwas microwaved at 120° C. for 1 h
  2. customReaction mixture
  3. customPrecipitate was collected
  4. customdried
  5. customThe crude product was triturated with MeOH (2 mL)
  6. customSolid was collected
  7. customdried in vacuo

Sources & evidence

ORD record
ord-34da44eec3d249d193a77820ae04f39f
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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