2,2-Dimethyl-beta-alanine → HCID 89812997, compound

HRID 1481084Notes

Reaction equation

HRID 1481084 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][C:27]([CH3:32])([CH3:31])[C:28]([OH:30])=[O:29].C[O-].[Na+].CO>>[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][C:27]([CH3:32])([CH3:31])[C:28]([OH:30])=[O:29])=[O:4])[N:6]=1)#[N:24]

Participants

4

Reactant 3

HCID 957392,2-Dimethyl-beta-alanineHCID 23694274Sodium methanolate methanolHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89812997HCID 89812997, compoundYield 51%

Procedure

A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (82 mg, 0.26 mmol) and 3-amino-2,2-dimethyl-propionic acid (90 mg, 0.77 mmol) (ChemBridge) in 0.5 M NaOMe/MeOH (1.0 mL, 0.5 mmol) was microwaved at 120° C. for 40 min. Reaction mixture was concentrated and the residue was dissolved in water (70 mL). It was acidified by 1 N HCl to pH=3-4. Precipitate was collected, rinsed with water and dried. Crude product was triturated with MeOH (2 mL). solid was collected and dried to provide the title compound 54.4 mg (0.13 mmol) in 51% yield. LC-MS ESI−: 404.03 (M−1)−.

Workup

  1. customwas microwaved at 120° C. for 40 min
  2. customReaction mixture
  3. concentrationwas concentrated
  4. dissolutionthe residue was dissolved in water (70 mL)
  5. customPrecipitate was collected
  6. washrinsed with water
  7. customdried
  8. customCrude product was triturated with MeOH (2 mL)
  9. customsolid was collected
  10. customdried

Sources & evidence

ORD record
ord-643e2be41ee745bfad40f7c0dc4fe467
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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