1,2-Dimethoxyethane → tert-butyl 4-(4-(2-acetamidobenzo[d]thiazol-4-yloxy)-6-(4-(trifluoromethyl)phenyl)pyrimidin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 2056701Notes

Reaction equation

HRID 2056701 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[C:14]3[N:15]=[C:16]([NH:18][C:19](=[O:21])[CH3:20])[S:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[N:3]=1.CC1(C)C(C)(C)OB([C:40]2[CH2:45][CH2:44][N:43]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:42][CH:41]=2)O1.C([O-])([O-])=O.[Na+].[Na+].O.C(COC)OC>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCO>[C:19]([NH:18][C:16]1[S:17][C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([O:8][C:6]3[CH:5]=[C:4]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)[N:3]=[C:2]([C:40]4[CH2:45][CH2:44][N:43]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:42][CH:41]=4)[N:7]=3)[C:14]=2[N:15]=1)(=[O:21])[CH3:20]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 2735133Sodium Carbonate MonohydrateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 58612070N-{4-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzo[d]thiazol-2-yl}-acetamide

Product 1

HCID 11692952tert-butyl 4-(4-(2-acetamidobenzo[d]thiazol-4-yloxy)-6-(4-(trifluoromethyl)phenyl)pyrimidin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

A mixture of N-{4-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzo[d]thiazol-2-yl}-acetamide (279 mg, 0.6 mmol, Example 7(d)), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (309 mg, 1.0 mmol, ChemShop), PdCl2(PPh3)2 (42 mg, 0.06 mmol, Aldrich), Na2CO3.H2O (74 mg, 0.6 mmol), dimethoxyethane (0.7 mL), H2O (0.3 mL) and EtOH (0.2 mL) was heated in a microwave synthesizer at 120° C. with stirring for 10 min. The reaction mixture was diluted with water (15 mL) and extracted with EtOAc (2×30 mL). The combined organic phases were washed with brine (20 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (30% EtOAc/hexane) to give the title compound. MS (ESI, pos. ion) m/z: 612 (M+1).

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined organic phases were washed with brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (30% EtOAc/hexane)

Sources & evidence

ORD record
ord-c9ea83912eb94cb2ace27a2c489e5143
Source dataset
uspto-grants-2008_02
Patent number
US07335672B2

Reaction notes

Loading…