4-(2-Aminoethyl)-2-chlorophenol → HCID 58603757, compound

HRID 2386584Notes

Reaction equation

HRID 2386584 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:16]=[N:17][CH:18]=[CH:19][CH:20]=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:16]=[N:17][CH:18]=[CH:19][CH:20]=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 86603256N-(3-(2-chloropyrimidin-4-yl)benzyl)-2-(pyridine-3-yl)ethanamine

Product 1

HCID 58603757HCID 58603757, compound

Procedure

Intermediate 172 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 8.50-8.43 (m, 2H) 8.29 (d, 1H) 8.21 (s, 1H), 8.1 (d, 1H), 7.7 (d, 1H) 7.63-7.55 (m, 2H), 7.42-7.38 (m, 1H), 7.19 (d, 1H) 7.09 (d, 1H), 6.99 (d, 1H), 6.8 (d, 1H), 4.2 (s, 2H), 3.6 (t, 2H), 3.3 (t, 2H), 3.0 (t, 2H), 2.8 (t, 2H).

Sources & evidence

ORD record
ord-2f21f89af1ed4a839133213bba059500
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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