Tetrahydrofuran → 2-(2-(3-(Morpholin-4-yl)-n-propyl)aminoanilin-4-yl)benzoxazole

HRID 74279Notes

Reaction equation

HRID 74279 reaction equation
N1(C(C)C[NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[O:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:12][C:11]=2[N+:25]([O-])=O)CCOCC1.[H][H].[O:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>[C].[Pd]>[N:9]1([CH2:10][CH2:11][CH2:12][NH:25][C:11]2[CH:12]=[C:13]([C:16]3[O:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[CH:14]=[CH:15][C:10]=2[NH2:9])[CH2:34][CH2:35][O:31][CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 674985632-(N-(2-(morpholin-4-yl)-n-propyl)-2-nitroanilin-4-yl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674982532-(2-(3-(Morpholin-4-yl)-n-propyl)aminoanilin-4-yl)benzoxazoleYield 99%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

To a solution of 2-(N-(2-(morpholin-4-yl)-n-propyl)-2-nitroanilin-4-yl)benzoxazole (see Working Example 96-1) (665 mg, 1.74 mmol) in tetrahydrofuran (10 mL) was added 10% palladium-carbon (70 mg). A hydrogen atmosphere was then substituted in the flask, and this was stirred at room temperature for 17 hours. After the reaction was finished, this was filtered through Celite, and the filtrate was concentrated to yield the title compound (605 mg, 99% yield).

Workup

  1. filtrationthis was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-29eb486814c94c0e888b39ee379cfbf7
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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