Hydrochloric Acid → HCID 71737377, compound

HRID 1481062Notes

Reaction equation

HRID 1481062 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]([CH2:31][CH3:32])[CH2:27][C:28]([OH:30])=[O:29].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][C@H:26]([CH2:31][CH3:32])[CH2:27][C:28]([OH:30])=[O:29])=[O:4])[N:6]=1)#[N:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14731979(3R)-3-Aminopentanoic acidHCID 23694274Sodium methanolate methanolHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 71737377HCID 71737377, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (75 mg, 0.234 mmol) and 3-(R)-amino-pentanoic acid (82 mg, 0.7 mmol) were placed in a CEM 10 mL Microwave vessel and sodium methoxide-methanol solution (0.5M; 1.4 mL, 0.7 mmol) was added via syringe. The vessel was sealed and heated to 130° C. in a CEM microwave apparatus for 150 minutes. The reaction mixture was diluted with water and treated with 1N hydrochloric acid. The crude precipitate was purified by MPLC (methylene chloride-ethyl acetate) to provide the title compound as an off-white solid in 73% yield. MS ESI(−) m/e: 403.9928 (M−1).

Workup

  1. additionwas added via syringe
  2. customThe vessel was sealed
  3. customThe crude precipitate was purified by MPLC (methylene chloride-ethyl acetate)

Sources & evidence

ORD record
ord-758ed70224924fa4aef0fb8b0feb546a
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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