3-Methoxytyramine → HCID 58603573, compound

HRID 14819Notes

Reaction equation

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

Participants

Reactant 2

HCID 16693-Methoxytyramine

HCID 249019832-Chloro-4-(4-isobutyl-phenyl)-pyrimidine

Product 1

HCID 58603573HCID 58603573, compound

Procedure

Intermediate 49 was coupled with 4-(2-Amino-ethyl)-2-methoxy-phenol following procedure F. LC-MS showed the product had the expected M+H+ of 378. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.3 (m, 1H) 7.99 (d, 2H) 7.25 (d, 2H) 6.95 (d, 1H) 6.85 (m, 1H) 6.74 (m, 2H) 5.5 (br s, 1H) 3.8 (s, 3H) 3.75 (m, 2H) 2.87 (t, 2H) 2.52 (t, 2H) 1.88 (m, 1H) 0.9 (d, 6H).

Sources & evidence

ORD record: ord-185e4150ee754aa5b7f166330eea629e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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