4-(2-Aminoethyl)-2-chlorophenol → 2-Chloro-4-[2-(4-{3-[(ethyl-piperidin-4-yl-amino)-methyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[CH:29]=[CH:28][N:27]=[C:26](Cl)[N:25]=3)[CH:19]=2)[CH2:15][CH3:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[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:26]2[N:25]=[C:24]([C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([CH2:17][N:14]([CH2:15][CH3:16])[CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:19]=3)[CH:29]=[CH:28][N:27]=2)[CH:39]=[CH:38][C:37]=1[OH:40]Participants
3
Procedure
Intermediate 84 was coupled with 4-(2-amino-ethyl)-2-chloro-phenol following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 467. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.27 (m, 2H), 7.69 (m, 2H), 7.26 (d, 1H), 7.19 (m, 1H), 7.04 (s, 1H), 7.01 (d, 1H), 6.80 (d, 1H), 4.48 (m, 2H), 3.53 (m, 4H), 3.09 (m, 4H), 2.85 (t, 2H), 2.39 (d, 2H), 2.03 (m, 3H), 1.32 (t, 3H).
Sources & evidence
- ORD record
- ord-fd0694ce9fe043ddb3326ef668a45f37
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732444B2
Reaction notes
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