N-(2-Fluoro-5-{2-[2-(3-Fluoro-4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-2-methoxy-benzyl)-N-piperidin-4-yl-methanesulfonamide → N-(2-Fluoro-5-{2-[2-(3-fluoro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-piperidin-4-yl-methanesulfonamide

HRID 2386473Notes

Reaction equation

HRID 2386473 reaction equation
[F:1][C:2]1(OC)[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32](O)=[C:31]([F:36])[CH:30]=3)[N:21]=2)=[CH:16][CH:3]1[CH2:4][N:5]([CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[S:6]([CH3:9])(=[O:8])=[O:7].C(OC(N1CCC(N(CC2C=C(C3C=CN=C(Cl)N=3)C=CC=2F)S(C)(=O)=O)CC1)=O)(C)(C)C>>[F:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:36])[CH:30]=3)[N:21]=2)=[CH:16][C:3]=1[CH2:4][N:5]([CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[S:6]([CH3:9])(=[O:7])=[O:8]

Participants

3

Reactant 2

HCID 67044948N-(2-Fluoro-5-{2-[2-(3-Fluoro-4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-2-methoxy-benzyl)-N-piperidin-4-yl-methanesulfonamideHCID 866032944-{[5-(2-Chloro-pyrimidin-4-yl)-2-fluoro-benzyl]-methanesulfonyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603621N-(2-Fluoro-5-{2-[2-(3-fluoro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-piperidin-4-yl-methanesulfonamide

Procedure

(N-(2-Fluoro-5-{2-[2-(3-Fluoro-4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-2-methoxy-benzyl)-N-piperidin-4-yl-methanesulfonamide: Intermediate 91 was coupled with intermediate 83 following procedure F. The resulting product was deprotected following procedure G. The product was purified by HPLC. LC-MS showed the product had the expected M+H+ of 518. 1H NMR (Varian 300 MHz, DMSO, shifts relative to the solvent peak at 2.50 ppm) δ 8.0 (d, 1H), 7.3-7.2 (m, 2H), 7.0 (m, 2H), 6.8 (m, 3H), 4.4 (s, 2H), 3.5 (d, 2H), 3.0 (s, 3H), 2.8-2.6 (m, 7H), 1.7 (m, 4H).

Workup

  1. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-e81b9682a1604cc3942270c5161d3bae
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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