N,N'-Dimethylethylenediamine → HCID 71617259, compound

HRID 626192Notes

Reaction equation

HRID 626192 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5](/[C:8](/[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[C:9](/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)\[CH2:10][CH3:11])=[CH:4][CH:3]=1.[CH3:25][NH:26][CH2:27][CH2:28][NH:29][CH3:30]>>[CH3:25][N:26]([CH2:27][CH2:28][NH:29][CH3:30])[C:2]1[N:7]=[CH:6][C:5](/[C:8](/[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[C:9](/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)\[CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8070N,N'-DimethylethylenediamineHCID 71617029HCID 71617029, compound

Product 1

HCID 71617259HCID 71617259, compound

Procedure

Following the same procedure as described in example 39, step D, (E)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol (100 mg, 1.0 eq, made from example 2) was reacted with N,N′-dimethylethane-1,2-diamine (262 mg, 10.0 eq) to give the desired product. 1H NMR (400 MHz, CDCl3) δ 8.07 (d, J=2.4 z, 1H), 7.06-7.14 (m, 6H), 6.69 (d, J=8.8 Hz, 2H), 6.49 (d, J=8.8 Hz, 1H), 6.43 (d, J=8.8 Hz, 2H), 3.71 (t, J=6.4 Hz, 2H), 3.08 (s, 3H), 2.88 (t, J=6.4 Hz, 2H), 2.53 (q, J=7.6 Hz, 2H), 2.48 (s, 3H), 0.95 (t, J=7.6 Hz, 3H); m/z=388[M+1]+.

Sources & evidence

ORD record
ord-a4290809067e4e1bb644e05e6066cb63
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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