Tyramine → HCID 58603543, compound

HRID 14965Notes

Reaction equation

HRID 14965 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][N:18]=[C:17](NCCC3C=CC=CC=3O)[N:16]=2)[CH:12]=[N:13][CH:14]=1.[Cl:31]C1N=C(C2C=C(CN3CCN(C(OC(C)(C)C)=O)C[C@@H]3C)C=NC=2)C=CN=1.[NH2:59][CH2:60][CH2:61][C:62]1[CH:67]=[CH:66][C:65]([OH:68])=[CH:64][CH:63]=1>>[Cl:31][C:64]1[CH:63]=[C:62]([CH2:61][CH2:60][NH:59][C:17]2[N:16]=[C:15]([C:11]3[CH:12]=[N:13][CH:14]=[C:9]([CH2:8][N:3]4[CH2:4][CH2:5][NH:6][CH2:7][C@@H:2]4[CH3:1])[CH:10]=3)[CH:20]=[CH:19][N:18]=2)[CH:67]=[CH:66][C:65]=1[OH:68]

Participants

4

Reactant 3

HCID 5610TyramineHCID 86603329HCID 86603329, compoundHCID 86603330HCID 86603330, compound

Product 1

HCID 58603543HCID 58603543, compound

Procedure

4-(2-(4-(5-(((S)-2-methylpiperazin-1-yl)methyl)pyridine-3-yl)pyrimidin-2-ylamino)ethylphenol: Intermediate 148 from above was coupled with tyramine following procedure F. The product was deprotected by procedure G2. LC-MS showed the product had the expected M+H+ of 405. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 9.4 (s, 1H) 9.0 (m, 2H) 8.5 (d, 1H) 7.5 (s, 1H), 7.0 (d, 2H), 6.6 (d, 2H), 3.7-3.5 (m, 5H) 3.4-3.3 (m, 6H), 2.8 (t, 2H), 1.6 (d, 3H).

Sources & evidence

ORD record
ord-ed9f4ecf52634036a5b50f35fe233586
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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