3-Methoxytyramine → HCID 58603758, compound

HRID 14821Notes

Reaction equation

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

Participants

Reactant 2

HCID 16693-Methoxytyramine

HCID 790791422-Chloro-4-(4-propoxy-phenyl)-pyrimidine

Product 1

HCID 58603758HCID 58603758, compound

Procedure

Intermediate 50 was coupled with 4-(2-Amino-ethyl)-2-methoxy-phenol following procedure F. LC-MS showed the product had the expected M+H+ of 380. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.0 (d, 1H), 7.1-7.0 (m, 4H) 6.8 (s, 1H), δ 6.7-6.6 (m, 3H), δ 4.0 (t, 2H), δ 3.7 (s, 3H), 3.5 (t, 2H), δ 2.7 (t, 2H), δ 1.8-1.7 (m, 2H), 0.9 (t, 3H).

Sources & evidence

ORD record: ord-3b2e3f9b875048f3be93257bebef8c2f
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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