HCID 58603398, compound → HCID 58603532, compound

HRID 2386469Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([O:36][CH3:37])=[C:22]([CH:35]=3)[CH2:23][N:24]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[S:25]([CH3:28])(=[O:27])=[O:26])[CH:15]=[CH:14][N:13]=2)[CH:5]=[CH:6][C:7]=1O.C(OC(N1CCC(N(CC2C=C(C3C=CN=C(Cl)N=3)C=CC=2OC)S(C)(=O)=O)CC1)=O)(C)(C)C>>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([O:36][CH3:37])=[C:22]([CH:35]=3)[CH2:23][N:24]([CH:29]3[CH2:30][CH2:31][NH:32][CH2:33][CH2:34]3)[S:25]([CH3:28])(=[O:26])=[O:27])[CH:15]=[CH:14][N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 58603398HCID 58603398, compound

HCID 866032924-{[5-(2-Chloro-pyrimidin-4-yl)-2-methoxy-benzyl]-methanesulfonyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603532HCID 58603532, compound

Procedure

(N-(5-{2-[2-(3-Fluoro-4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-2-methoxy-benzyl)-N-piperidin-4-yl-methanesulfonamide: Intermediate 88 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 530. 1H NMR (Varian 300 MHz, DMSO, shifts relative to the solvent peak at 2.50 ppm) δ 7.9 (d, 1H), 7.0 (m, 2H), 7.0 (m, 3H), 6.8 (m, 2H), 4.3 (s, 2H), 3.9 (s, 3H), 3.5 (d, 2H), 3.0 (s, 3H), 2.7 (m, 6H), 2.6 (m, 1H), 1.7-1.5 (m, 4H).

Workup

customThe product was purified by HPLC

Sources & evidence

ORD record: ord-675bc0759e2e42589748fb4f032131a9
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268822B2

Reaction notes

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