Hydrochloric Acid → HCID 89813077, compound

HRID 1481202Notes

Reaction equation

HRID 1481202 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([C:26]#[N:27])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH:12]=2)=[O:7])CCC.[NH2:28][CH2:29][C:30]1([C:34]([OH:36])=[O:35])[CH2:33][CH2:32][CH2:31]1.C[O-].[Na+].CO.Cl>O>[C:26]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([NH:28][CH2:29][C:30]2([C:34]([OH:36])=[O:35])[CH2:33][CH2:32][CH2:31]2)=[O:7])[N:9]=1)#[N:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 23405971HCID 23405971, compoundHCID 23694274Sodium methanolate methanolHCID 89813208HCID 89813208, compound

Product 1

HCID 89813077HCID 89813077, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-cyano-7-cyclohexyloxy-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (20 mg, 0.054 mmol) and 1-aminomethyl-cyclobutanecarboxylic acid (37 mg, 0.22 mmol) in 0.5 M NaOMe/MeOH solution (0.84 mL, 0.42 mmol) was microwaved at 120° C. for 2 h. Reaction mixture was diluted with water (50 mL) and acidified by 1 N HCl to pH=3-4. Precipitate was collected, rinsed with water and dried. Crude product was purified by silica gel chromatography, eluting with 10-100% EtOAc/hexanes, to provide the title compound 8 mg (0.019 mmol) in 35% yield. LC-MS ESI−: 422.03 (M−1)−.

Workup

  1. customwas microwaved at 120° C. for 2 h
  2. customReaction mixture
  3. customPrecipitate was collected
  4. washrinsed with water
  5. customdried
  6. customCrude product was purified by silica gel chromatography
  7. washeluting with 10-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-1f7f7f933f1c49098451b2d0274f24f4
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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