Hydrochloric Acid → HCID 18687422, compound

HRID 1872709Notes

Reaction equation

HRID 1872709 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][CH3:13])[CH:3]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:36][C:37]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:38]=1[CH2:39][CH2:40][N:41]([CH3:47])[CH2:42]2.Cl>CN(C=O)C.CO.ClCCl>[ClH:11].[CH3:47][N:41]1[CH2:40][CH2:39][C:38]2[C:43](=[CH:44][CH:45]=[CH:46][C:37]=2[NH:36][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([Cl:11])[C:2]([NH2:1])=[CH:3][C:4]=2[O:12][CH3:13])[CH2:42]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 141712692-Methyl-1,2,3,4-tetrahydroisoquinolin-5-amine

Product 1

HCID 18687422HCID 18687422, compoundYield 36.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-Amino-5-chloro-2-methoxybenzoic acid (2.08 g, 11.1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.77 g 9.24 mmol) and 1-hydroxybenzotriazole (1.25 g, 9.24 mmol) were dissolved in dry DMF (40 ml) and stirred at room temperature under argon for 0.5h before 5-amino-2-methyl-1,2,3,4-tetrahydroisoquinoline (1.5 g, 9.24 mmol) was added. The mixture was then stirred for 18 h under argon at room temperature. The DMF was removed in vacuo and the residue taken up into ethyl acethate and washed with water, saturated aqueous sodium bicarbonate and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford a yellow solid. This was then passed through a short pad of silica eluting with dichloromethane to afford a white solid which was then taken up into methanol and treated with hydrogen chloride (1M in ether, 1 equivalent). The solvent was removed in vacuo and the residue recrystallised from methanol and ethyl acethate to afford the title compound as a white solid (0.775 g).

Workup

  1. additionwas added
  2. customThe DMF was removed in vacuo
  3. washwashed with water, saturated aqueous sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford a yellow solid
  7. customto afford a white solid which
  8. customThe solvent was removed in vacuo
  9. customthe residue recrystallised from methanol and ethyl

Sources & evidence

ORD record
ord-f3568f25edc444fd8c95cc9636cc825c
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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