1,2,3,4-Tetrahydroisoquinoline → HCID 45275803, compound

HRID 1667082Notes

Reaction equation

HRID 1667082 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[O:11]=[C:12]1[C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:14][N:13]1[CH2:29][C:30](O)=[O:31].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:30](=[O:31])[CH2:29][N:13]1[CH2:14][CH2:15][C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12]1=[O:11]

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45275803HCID 45275803, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,2,3,4-tetrahydroisoquinoline (0.025 g, 0.186 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.050 g, 0.169 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.049 g, 0.254 mmol) in dichloromethane (0.5 mL) was stirred at room temperature. After stirring overnight, the reaction was loaded directly onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 0.4% to 4.5% methanol/dichloromethane over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.15-7.40 (m, 14H), 4.55-4.80 (m, 2H), 4.25 (s, 2H), 3.60-3.85 (m, 2H), 3.45-3.55 (m, 2H), 2.70-2.90 (m, 4H); MS (ESI+) m/z 411 (M+H)+.

Workup

  1. washthe title compound was eluted
  2. customover 20 minutes

Sources & evidence

ORD record
ord-5a331b2933cd4cd8a46c962e8381afd1
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

Loading…