Dimethylformamide → HCID 69216313, compound

HRID 2222035Notes

Reaction equation

HRID 2222035 reaction equation
Cl[CH2:2][C:3]1[CH:28]=[CH:27][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])=[C:5]([O:29][CH3:30])[CH:4]=1.[OH:31][C:32]1[C:36](/[CH:37]=[CH:38]/[C:39]2[N:40]=[C:41]([N:45]3[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:47][CH2:46]3)[S:42][C:43]=2[CH3:44])=[CH:35][N:34]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[N:33]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:11]2[O:12][C:13]([CH3:14])=[C:9]([CH2:8][O:7][C:6]3[CH:27]=[CH:28][C:3]([CH2:2][O:31][C:32]4[C:36](/[CH:37]=[CH:38]/[C:39]5[N:40]=[C:41]([N:45]6[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:47][CH2:46]6)[S:42][C:43]=5[CH3:44])=[CH:35][N:34]([C:58]5[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=5)[N:33]=4)=[CH:4][C:5]=3[O:29][CH3:30])[N:10]=2)=[CH:20][CH:19]=1)[CH3:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 86605724Ethyl (4-{4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}phenyl)acetateHCID 178435094HCID 178435094, compound

Product 1

HCID 69216313HCID 69216313, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl (4-{4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}phenyl)acetate (0.66 g), tert-butyl 4-{4-[(E)-2-(3-hydroxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-5-methyl-1,3-thiazol-2-yl}piperazine-1-carboxylate (0.81 g), potassium carbonate (0.22 g) and N,N-dimethylformamide (20 mL) was stirred at 90° C. for 1 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with tetrahydrofuran-hexane (1:5, v/v) to give tert-butyl 4-{4-[(E)-2-(3-{[4-({2-[4-(2-ethoxy-2-oxoethyl)phenyl]-5-methyl-1,3-oxazol-4-yl}methoxy)-3-methoxybenzyl]oxy}-1-phenyl-1H-pyrazol-4-yl)ethenyl]-5-methyl-1,3-thiazol-2-yl}piperazine-1-carboxylate as crystals (0.53 g, yield 41%). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 112-114° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with tetrahydrofuran-hexane (1:5

Sources & evidence

ORD record
ord-989ba2047160418d95810a259abf9523
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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