Tetrahydrofuran → HCID 66816934, compound

HRID 1697108Notes

Reaction equation

HRID 1697108 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]3[C:29]([CH3:30])=[CH:28][CH:27]=[C:26]3[CH3:31])[N:20]=2)[CH:3]=1.C[Si]([N-:36][Si](C)(C)C)(C)C.[Na+].[CH2:42]1[CH2:46][O:45][CH2:44][CH2:43]1>CN(C=O)C.CCOC(C)=O.O>[CH2:10]([C:9]1[C:8](=[O:17])[C:5]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]3[C:26]([CH3:31])=[CH:27][CH:28]=[C:29]3[CH3:30])[N:20]=2)[C:43]=1[C:44]1[O:45][CH:46]=[CH:42][N:36]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 66815805HCID 66815805, compound

Product 1

HCID 66816934HCID 66816934, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 22728543Water ethylacetateSolvent

Procedure

A mixture of oxazole-2-carboxylic acid (147 mg) and DMF (2 drops) in DCM (1 mL) was treated with oxalyl chloride (127 μL). Gas evolution ceased after 2 h. CHCl3 (2 mL) was added, the volatiles removed in a vacuum oven (40° C., 200 mbar), and the residual oil dissolved in THF (2 mL) to form “solution A”. A mixture of 1-{4-chloro-2-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-ylamino]-phenyl}-3-phenyl-propan-1-one (430 mg) in THF (2 mL) was treated with DMF (2 drops) and NaHMDS solution (2.5 mL, 1 M in THF) was added dropwise. Solution A (2 mL) was added dropwise, and the mixture stirred at RT for 12 h. The product was worked up in EtOAc/H2O and chromatographed (DCM/MeOH 100:0 to 70:30) to provide 3-benzyl-7-chloro-1-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-yl]-2-oxazol-2-yl-1H-quinolin-4-one.

Workup

  1. additionwas added dropwise
  2. customchromatographed (DCM/MeOH 100:0 to 70:30)

Sources & evidence

ORD record
ord-0780150555c548c2b3e5868d3052dd04
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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