2-Aminoindane → HCID 45275802, compound

HRID 1667085Notes

Reaction equation

HRID 1667085 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH2:10].[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:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][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 763102-AminoindaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45275802HCID 45275802, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,3-dihydro-1H-inden-2-amine (0.020 g, 0.149 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.040 g, 0.135 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.039 g, 0.203 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 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.18-7.32 (m, 14H), 6.05 (d, J=7.5 Hz, 1H), 4.60 (qt, J=7.5, 5.7 Hz, 1H), 3.99 (s, 2H), 3.49 (t, J=6.5 Hz, 2H), 3.20 (dd, J=15.9, 7.5 Hz, 2H), 2.78 (t, J=6.5 Hz, 2H), 2.52 (dd, J=15.9, 5.8 Hz, 2H); MS (ESI−) m/z 409 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-36473302ea38404fab293b3fdf0499a4
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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