1-Hydroxybenzotriazole → HCID 58778945, compound

HRID 1372724Notes

Reaction equation

HRID 1372724 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[C:12]([OH:14])=O)=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][C:17]=1[Cl:27].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:27][C:17]1[CH:18]=[C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:20]=[CH:21][C:16]=1[NH:15][C:12]([C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=2)[CH:6]=[CH:7][N:8]=1)=[O:14]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetateHCID 17859248HCID 17859248, compound

Product 1

HCID 58778945HCID 58778945, compoundYield 51.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In DMF (5 ml) were dissolved 7-fluoro-1-isoquinolinecarboxylic acid (250 mg, 1.31 mmol), methyl 4-amino-3-chlorophenylacetate (262 mg, 1.31 mmol), HOBt (catalytic amount), and DMAP (192 m g, 1.57 mmol). To the resulting solution was added EDC HCl (290 mg, 6.93 mmol), followed by stirring at room temperature for 14 hours. The reaction mixture was poured into water (20 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with ether and then dried under reduced pressure to give methyl (3-chloro-4-((7-fluoro-1-isoquinolinylcarbonyl)amino)phenyl)acetate (250 mg, 51%) as a colorless crystalline powder.

Workup

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

Sources & evidence

ORD record
ord-9223936bfeca43749140ddc818aefe5f
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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