4-(2-Aminoethyl)-2-chlorophenol → 2-Chloro-4-(2-{4-[3-(2(S)-methyl-piperidin-1-ylmethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

HRID 14884Notes

Reaction equation

HRID 14884 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]3[CH3:21])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([Cl:32])[CH:26]=1>>[Cl:32][C:27]1[CH:26]=[C:25]([CH2:24][CH2:23][NH:22][C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]4[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]4[CH3:21])[CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:30]=[CH:29][C:28]=1[OH:31]

Participants

3

Reactant 2

HCID 230715554-(2-Aminoethyl)-2-chlorophenolHCID 866033022-Chloro-4-[3-(2-methyl-piperidin-1-ylmethyl)-phenyl]-pyrimidine

Product 1

HCID 586035842-Chloro-4-(2-{4-[3-(2(S)-methyl-piperidin-1-ylmethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

Procedure

Intermediate 108 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 438. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.29 (d, 1H), 8.24 (s, 1H), 8.00 (d, 1H), 7.61 (d, 1H), 7.44 (t, 1H), 7.15 (s, 1H), 7.08 (d, 1H), 6.93 (d, 1H), 6.84 (d, 1H), 5.37 (t, 1H), 4.36 (d, 1H), 3.75 (d, 1H), 3.66 (m, 2H), 2.93 (m, 2H), 2.80 (t, 2H), 2.42 (s, 1H), 1.75 (m, 5H), 1.38 (m, 4H).

Sources & evidence

ORD record
ord-6ad95e9134b14f978523f9ec090586d9
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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