Tyramine → HCID 58603756, compound

HRID 2386376Notes

Reaction equation

HRID 2386376 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:22]=[CH:23][CH:24]=2)[CH2:11][N:12]([CH2:20][CH3:21])[CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[CH:4][N:3]=1.[NH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1>>[CH2:20]([N:12]([CH2:11][C:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=3)[N:7]=2)[CH:24]=[CH:23][CH:22]=1)[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH3:21]

Participants

3

Reactant 2

HCID 5610TyramineHCID 86603260[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-pyridin-3-ylmethyl-amine

Product 1

HCID 58603756HCID 58603756, compound

Procedure

Intermediate 23 was coupled with tyramine following procedure F. LC-MS showed the product had the expected M+H+ of 440. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.63 (s, 1H) 8.49 (m, 1H) 8.26 (m, 1H) 8.15 (s, 1H) 8.05 (s, 1H) 7.45 (m, 2H) 7.25 (m, 1H) 7.05 (m, 3H) 6.99 (d, 1H) 6.75 (m, 4H) 3.4-3.8 (m, 4H) 2.88 (t, 2H) 2.75 (t, 2H) 2.55 (m, 2H) 1.05 (t, 3H).

Sources & evidence

ORD record
ord-3e82b2126400458d95071f1989c94f43
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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