4-(2-Aminoethyl)-2-chlorophenol → HCID 58603745, compound

HRID 14964Notes

Reaction equation

HRID 14964 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[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]=[CH:4][N:3]=1.[NH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([Cl:41])[CH:35]=1>>[Cl:41][C:36]1[CH:35]=[C:34]([CH2:33][CH2:32][NH:31][C:2]2[N:7]=[C:6]([C:8]3[CH:9]=[C:10]([CH2:11][N:12]4[CH2:17][CH2:16][NH:15][CH2:14][C@@H:13]4[CH3:25])[CH:26]=[CH:27][C:28]=3[O:29][CH3:30])[CH:5]=[CH:4][N:3]=2)[CH:39]=[CH:38][C:37]=1[OH:40]

Participants

3

Reactant 2

HCID 230715554-(2-Aminoethyl)-2-chlorophenolHCID 86603328HCID 86603328, compound

Product 1

HCID 58603745HCID 58603745, compound

Procedure

Intermediate 146 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 468. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.4 (d, 1H) 7.8 (d, 1H) 7.4-7.2 (m, 3H) 7.1 (m, 2H), 6.1 (d, 1H), 3.9 (s, 3H) 3.7-3.6 (m, 4H) 3.5 (d, 2H) 3.4-3.3 (m, 4H), 3.2 (m, 1H), 2.8 (t, 2H), 1.6 (d, 3H).

Sources & evidence

ORD record
ord-cb1bc70003fd4c389b1f49b655b5505d
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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