Dichloromethane → HCID 86759566, compound

HRID 2416591Notes

Reaction equation

HRID 2416591 reaction equation
C([NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([I:21])=[C:16]([O:19][CH3:20])[CH:17]=2)[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1.ClC[CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+].ClCCl>C(O)(=O)C.Br>[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([I:21])=[C:16]([O:19][CH2:20][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:17]=2)[CH:12]=[CH:11][N:10]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 3795708N-Boc-2-chloroethylamineHCID 22631323HCID 22631323, compound

Product 1

HCID 86759566HCID 86759566, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Conditions

Temperature
140 °C

Procedure

10.4 g (26.7 mmol) of benzyl-(6-iodo-7-methoxyisoquinoline-1-yl)amine was dissolved in a mixture of 8 ml of acetic acid and 40 ml of hydrobromic acid, and the obtained solution was stirred at 140° C. overnight. The solvent was evaporated, and the residue was dissolved in 50 ml of DMF. 14.6 g (65.2 mmol) of t-butyl (2-chloroethyl)carbamate and 4.95 g (163 mmol) of potassium carbonate were added to the obtained solution, and they were stirred at 70° C. overnight. After the treatment with dichloromethane as the extraction solvent in an ordinary manner, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 50 ml of DMF
  3. stirringwere stirred at 70° C. overnight
  4. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-b5583d9f791a45c0be443de05d2d5d5a
Source dataset
uspto-grants-2004_11
Patent number
US06825181B1

Reaction notes

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