4-(2-Aminoethyl)-2-chlorophenol → (3-{2-[2-(3-Chloro-4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-isopropyl-carbamic acid tert-butyl ester

HRID 14846Notes

Reaction equation

HRID 14846 reaction equation
[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=2)[CH:13]=1)[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[NH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([Cl:36])[CH:30]=1>>[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([Cl:36])[CH:30]=3)[N:19]=2)[CH:13]=1)[CH:8]([CH3:9])[CH3:10])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 230715554-(2-Aminoethyl)-2-chlorophenolHCID 86603285[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-isopropyl-carbamic acid tert-butyl ester

Product 1

HCID 67044858(3-{2-[2-(3-Chloro-4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-isopropyl-carbamic acid tert-butyl ester

Procedure

Intermediate 70 was coupled with Intermediate 71 following procedure F. LC-MS showed the product had the expected M+H+ of 497. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.3 (d, 1H) 7.9 (m, 2H) 7.4 (m, 2H) 7.2 (m, 2H) 7.0 (m, 3H) 4.4 (s, 2H) 3.7 (m, 2H) 2.8 (m, 2H) 1.4 (s, br, 10H) 1.0 (d, 6H).

Sources & evidence

ORD record
ord-20fb1a096b914439ad7aeb0dd24776c2
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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