N,N-Dimethylglycine → HCID 178483933, compound

HRID 2236890Notes

Reaction equation

HRID 2236890 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][CH:8]=[C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([I:19])[CH:17]=3)[C:12](=[O:20])[NH:11][C:10]2=[O:21])=[CH:4][C:3]=1[OH:24].C(N(CC)CC)C.[CH3:32][N:33]([CH2:35][C:36](O)=[O:37])[CH3:34].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[OH:24][C:3]1[CH:4]=[C:5]([CH2:6][NH:7]/[CH:8]=[C:9]2\[C:10](=[O:21])[NH:11][C:12](=[O:20])[C:13]3[C:18]\2=[CH:17][C:16]([I:19])=[CH:15][CH:14]=3)[CH:22]=[CH:23][C:2]=1[NH:1][C:36](=[O:37])[CH2:35][N:33]([CH3:34])[CH3:32]

Participants

7

Reactant 5

HCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178507623HCID 178507623, compound

Product 1

HCID 178483933HCID 178483933, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[(4-Amino-3-hydroxy-benzylamino)-methylene]-6-iodo-4H-isoquinoline-1,3-dione (89 mg, 0.20 mmol) is dissolved in N,N-dimethylformamide (3.56 mL), followed by addition of triethylamine (0.236 mL, 1.69 mmol), dimethylamino-acetic acid (30.58 mg, 0.30 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodimide hydrochloride (42.6 mg, 0.22 mmol) and 1-hydroxybenzotriazole (13.8 mg, 0.10 mmol). It is stirred at room temperature overnight. It is then evaporated to dryness, and the residue is washed with ether, and then acetonitrile to yield 21 mg (20%) of the title compound as a solid. MS (ESI) m/z 521 (M+H)+1

Workup

  1. customIt is then evaporated to dryness
  2. washthe residue is washed with ether

Sources & evidence

ORD record
ord-a3602823b1b84b189395e222440501be
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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