4-(2-Aminoethyl)-2-chlorophenol → HCID 58603575, compound

HRID 14967Notes

Reaction equation

HRID 14967 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:26]=[CH:27][CH:28]=2)[CH2:11][N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C@@H:13]2[CH3:25])[CH:5]=[C:4]([CH3:29])[N:3]=1.[NH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([Cl:40])[CH:34]=1>>[Cl:40][C:35]1[CH:34]=[C:33]([CH2:32][CH2:31][NH:30][C:2]2[N:3]=[C:4]([CH3:29])[CH:5]=[C:6]([C:8]3[CH:28]=[CH:27][CH:26]=[C:10]([CH2:11][N:12]4[CH2:17][CH2:16][NH:15][CH2:14][C@@H:13]4[CH3:25])[CH:9]=3)[N:7]=2)[CH:38]=[CH:37][C:36]=1[OH:39]

Participants

3

Reactant 2

HCID 230715554-(2-Aminoethyl)-2-chlorophenolHCID 87247342HCID 87247342, compound

Product 1

HCID 58603575HCID 58603575, compound

Procedure

Intermediate 150 from above was coupled with 4-(2-aminoethyl)-2-chlorophenol following procedure F. The product was deprotected by procedure G2. LC-MS showed the product had the expected M+H+ of 452. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.6 (d, 1H) 8.3 (d, 1H) 7.9 (d, 1H) 7.7 (t, 1H), 7.5 (s, 1H), 7.2 (s, 1H), 7.0 (d, 1H), 6.8 (d, 1H), 4.12-3.9 (m, 5H) 3.8-3.47 (m, 6H), 2.9 (t, 2H), 2.6 (s, 3H), 1.6 (d, 3H).

Sources & evidence

ORD record
ord-5a6d958089c14f78856c85307b2b787f
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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