Hydroxylamine → HCID 86650345, compound

HRID 1186694Notes

Reaction equation

HRID 1186694 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:24]=[C:25]([C:29]2[C:30]([C:35](OCC)=O)=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:26]=[CH:27][CH:28]=1)=O)=O)(C)(C)C.[OH-:40].[K+].[NH2:42][OH:43].[OH2:44]>CO.C1COCC1.C([O-])(O)=O.[Na+]>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:24]=[C:25]([C:29]2[C:30]([C:35]([NH:42][OH:43])=[O:44])=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:26]=[CH:27][CH:28]=1)=[O:40]

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 962WaterHCID 14797Potassium HydroxideHCID 66863843HCID 66863843, compound

Product 1

HCID 86650345HCID 86650345, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of ethyl 3′-(2-amino-5-(thiophen-2-yl)phenylcarbamoyl)biphenyl-2-carboxylate 62 (0.195 g, 0.441 mmol), in methanol (1.102 ml) and THF (1.102 ml), potassium hydroxide (0.220 ml, 0.881 mmol) was added followed by a 50% hydroxylamine solution in water (1.455 g, 22.03 mmol). The mixture was stirred at rt for 18 h. It was then diluted with aqueous NaHCO3, and extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (15% MeOH/DCM) to afford title compound 63 (0.04 g, 21% yield) as a white solid. 1H NMR: (DMSO) d(ppm) 1H, 10.80 (s, 1H), 9.80 (s, 1H), 9.01 (s, 1H), 8.04 (s, 1H), 7.98 (d, 1H), 7.55 (m, 5H), 7.44 (m, 2H), 7.35 (d, 1H), 7.30 (dd, 1H), 7.25 (d, 1H), 7.04 (m, 1H), 6.82 (d, 1H), 5.18 (s, 2H). LRMS (ESI): (calc.) 429.49 (found) 430.2 (MH)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (15% MeOH/DCM)

Sources & evidence

ORD record
ord-b5ed68a29699441e8f4ab063f1fc576c
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

Loading…