Dimethylformamide → HCID 67161596, compound

HRID 469525Notes

Reaction equation

HRID 469525 reaction equation
[C:1]1([C:7]2[C:12]3[S:13][CH:14]=[CH:15][C:11]=3[C:10](=[O:16])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC([O-])(C)C.[K+].C1(P(O[NH2:38])(C2C=CC=CC=2)=O)C=CC=CC=1.CN(C=O)C>C1COCC1.CCOC(C)=O>[NH2:38][N:9]1[C:10](=[O:16])[C:11]2[CH:15]=[CH:14][S:13][C:12]=2[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 12796522HCID 12796522, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 67161596HCID 67161596, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 9A (69.1 mg, 0.303 mmol) and KOtBu (1 M in THF, 0.35 mL, 0.35 mmol) in THF (1.5 mL) was stirred for 60 min, and O-(diphenylphosphoryl)hydroxylamine (81.0 mg, 0.348 mmol) and DMF (1.5 mL) were added and stirred 1 hour. The mixture was diluted with EtOAc, washed with 1 N NaOH and water, dried (Na2SO4), filtered, and concentrated to give the title compound as a white solid (62.6 mg), which was used without purification. 1H NMR (300 MHz, DMSO-d6) δ 8.16 (d, 1H), 7.89-7.82 (m, 2H), 7.75 (d, 1H), 7.64-7.51 (m, 3H), 6.65 (s, 2H); LC/MS (APCI) M/Z 244.1 (M+H)+.

Workup

  1. washwashed with 1 N NaOH and water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2a6293cc9c3f4952be35bd473b96f05e
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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