4-(2-Aminoethyl)-2-chlorophenol → 2-Chloro-4-(2-(4-(3-((2-(pyridine-4-yl)ethylamino)methyl)phenyl)pyrimidin-2-ylamino)ethyl)phenol

HRID 14985Notes

Reaction equation

HRID 14985 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=2)[CH2:11][NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:5]=[CH:4][N:3]=1.[NH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([Cl:34])[CH:28]=1>>[Cl:34][C:29]1[CH:28]=[C:27]([CH2:26][CH2:25][NH:24][C:2]2[N:7]=[C:6]([C:8]3[CH:23]=[CH:22][CH:21]=[C:10]([CH2:11][NH:12][CH2:13][CH2:14][C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)[CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:32]=[CH:31][C:30]=1[OH:33]

Participants

3

Reactant 2

HCID 230715554-(2-Aminoethyl)-2-chlorophenolHCID 86603257N-(3-(2-chloropyrimidin-4-yl)benzyl)-2-(pyridine-4-yl)ethanamine

Product 1

HCID 586035992-Chloro-4-(2-(4-(3-((2-(pyridine-4-yl)ethylamino)methyl)phenyl)pyrimidin-2-ylamino)ethyl)phenol

Procedure

Intermediate 173 from above was coupled with 4-(2-aminoethyl)-2-chlorophenol following procedure F. LC-MS showed the product had the expected M+H+ of 460. 1H NMR (Varian 300 MHz, MeOD-d6, shifts relative to the solvent peak at 3.31 ppm) δ 8.4 (d, 2H) 8.4 (s, 1H) 8.29 (d, 1H), 8.25 (s, 1H), 8.15 (d, 1H) 7.66-7.56 (m, 2H), 7.36 (d, 1H), 7.20 (d, 1H) 7.10 (d, 1H), 7.0 (d, 1H), 6.8 (d, 1H), 4.3 (s, 2H), 3.6 (t, 2H), 3.3 (t, 2H), 3.0 (t, 2H), 2.8 (t, 2H).

Sources & evidence

ORD record
ord-92be7cb1f21b414d9071a2404882f0be
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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