Isoquinoline-1-carboxylic acid → HCID 58778725, compound

HRID 1372721Notes

Reaction equation

HRID 1372721 reaction equation
[C:1]1([C:11]([OH:13])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][C:16]=1[Cl:26].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[Cl:26][C:16]1[CH:17]=[C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:20][C:15]=1[NH:14][C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1)=[O:13]

Participants

8

Reactant 4

HCID 68092Isoquinoline-1-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Product 1

HCID 58778725HCID 58778725, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In DMF (15 ml) were dissolved 1-isoquinolinecarboxylic acid (1.00 g, 5.77 mmol), methyl 4-amino-3-chlorophenylacetate (1.23 g, 6.16 mmol), HOBt (0.16 g, 1.15 mmol), and DMAP (0.14 g, 1.15 mmol). To the resulting solution was added EDC HCl (1.33 g, 6.93 mmol), followed by stirring at room temperature for 14 hours. The reaction mixture was poured into water (40 ml). The crystals precipitated were collected by filtration under reduced pressure, washed with water and ether, dried under reduced pressure to give methyl (3-chloro-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetate (1.14 g, 56%) as a brown solid.

Workup

  1. customThe crystals precipitated
  2. filtrationwere collected by filtration under reduced pressure
  3. washwashed with water and ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-9018fece3b2d47d187e2f2e3aff3ddfa
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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