HCID 86712647, compound → tert-Butyl 4-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoyl)piperazine-1-carboxylate

HRID 1778982Notes

Reaction equation

HRID 1778982 reaction equation
[CH3:1][O:2][C:3](=[O:45])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]#[C:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]2[CH:44]=[CH:43][C:27]([C:28]([N:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]3)=[O:29])=[CH:26][CH:25]=2)[N:14]=1>[Pd].CCN(CC)CC>[CH3:1][O:2][C:3](=[O:45])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH2:12][C:13]1[C:18]([C:19]([F:21])([F:22])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]2[CH:44]=[CH:43][C:27]([C:28]([N:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]3)=[O:29])=[CH:26][CH:25]=2)[N:14]=1

Participants

4

Reactant 1

HCID 86712647HCID 86712647, compound

Product 1

HCID 86712648tert-Butyl 4-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A suspension of 10% Pd/C (53% water; 0.660 g), tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoyl)piperazine-1-carboxylate (A23) (0.337 g, 0.540 mmol) and Et3N (1 mL) was stirred at room temperature for 16 hours under an atmosphere of hydrogen. The mixture was filtered through a pad of Celite, washing with EtOAc (80 mL). The filtrates were evaporated in vacuo affording a yellow oil which was purified by silica gel column chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-80% EtOAc in petroleum benzine 40-60° C.) to yield the title compound A24 as a pale yellow oil (0.245 g, 72%); 1H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 8.19 (s, 1H), 7.72 (d, J=8.7 Hz, 2H), 7.41 (d, J=8.6 Hz, 2H), 7.25-7.13 (m, 4H), 3.73 (s, 2H), 3.65 (s, 3H), 3.84-3.30 (m, 8H), 3.18-3.00 (m, 4H), 1.46 (s, 9H). LCMS-A: rt 6.500 min; m/z 628 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashing with EtOAc (80 mL)
  3. customThe filtrates were evaporated in vacuo
  4. customaffording a yellow oil which
  5. customwas purified by silica gel column chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-80% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-f5bc3baececb4f3b8ae33820048e143e
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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