Potassium Hydroxide → HCID 72330477, compound

HRID 2098583Notes

Reaction equation

HRID 2098583 reaction equation
Cl.[NH2:2][OH:3].[OH-].[K+].[CH:6]1([NH:9][C:10](=[O:38])[C:11]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[CH:12][C:13]2[CH:30]=[CH:29][C:16]([C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](OC)=[O:26])=[O:18])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1>CO.C(Cl)Cl.O>[CH:6]1([NH:9][C:10](=[O:38])[C:11]([C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)=[CH:12][C:13]2[CH:30]=[CH:29][C:16]([C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([NH:2][OH:3])=[O:26])=[O:18])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 68418781HCID 68418781, compound

Product 1

HCID 72330477HCID 72330477, compoundYield 22.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Hydroxylamine hydrochloride (0.55 g, 8 mmol) in methanol (3 mL) was mixed with KOH (0.45 g, 8 mmol) in methanol (3 mL) at 0° C., and sonicated for 2 minutes and the white precipitate formed was filtered. The filtrate was added to the methyl 6-(4-(3-(cyclopropylamino)-2-(4-fluorophenyl)-3-oxoprop-1-enyl)benzamido)hexanoate (0.2 g, 0.4 mmol) in DCM (1.5 mL) and the mixture was stirred at room temperature, for 30 minutes. The reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (3×100 mL). The ethyl acetate layer was washed with water (100 mL), dried over anhydrous Na2SO4 and concentrated to afford the title compound (0.040 g, 20% yield). 1H NMR (DMSO-d6) δ (ppm): 0.52 (2H, m, 0.63-0.64 (2H, m, —CH2), 1.23-1.25 (2H, m, CH2), 1.44-1.50 (4H, m, CH2), 1.90-1.94 (2H, m, CH2), 2.74-2.75 (1H, m, —CH), 3.17-3.19 (2H, m, CH2), 7.04 (2H, d, Ar—H), 7.16-7.22 (4H, m, Ar—H), 7.28 (1H, s, ═C), 7.63 (2H, d, Ar—H), 7.89 (1H, d, NH), 8.36 (1H, t, NH), 8.66 (1H, s, —OH), 10.32 (1H, s, NH), MS m/z: 452.2 (M+−1).

Workup

  1. customsonicated for 2 minutes
  2. customthe white precipitate formed
  3. filtrationwas filtered
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washThe ethyl acetate layer was washed with water (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1626af542fd04996890a8caf911c86e2
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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