Tyramine → HCID 58603511, compound

HRID 14900Notes

Reaction equation

HRID 14900 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]3[CH3:21])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1>>[CH3:21][C@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20][N:15]1[CH2:14][C:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)[N:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 5610TyramineHCID 866033022-Chloro-4-[3-(2-methyl-piperidin-1-ylmethyl)-phenyl]-pyrimidine

Product 1

HCID 58603511HCID 58603511, compound

Procedure

Intermediate 108 was coupled with tyramine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 404. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.26 (d, 1H), 7.93 (s, 1H), 7.86 (d, 1H), 7.36 (m, 2H), 6.99 (d, 2H), 6.92 (d, 1H), 6.63 (d, 2H), 5.26 (t, 1H), 4.05 (d, 1H), 3.70 (d, 2H), 3.28 (d, 1H), 2.75 (m, 4H), 2.37 (s, 1H), 1.63 (m, 2H), 1.39 (m, 3H), 1.20 (m, 4H).

Sources & evidence

ORD record
ord-326a627d5db74315add94381b947d8a8
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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