Potassium Hydroxide → HCID 86647576, compound

HRID 2098571Notes

Reaction equation

HRID 2098571 reaction equation
Cl.[NH2:2][OH:3].[OH-].[K+].[CH:6]1([NH:9][C:10](=[O:40])[C:11]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[CH:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH:28][C:29](OC)=[O:30])=[O:22])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1>CO.C(Cl)Cl.O>[CH:6]1([NH:9][C:10](=[O:40])/[C:11](/[C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[CH:12]/[C:13]2[CH:14]=[CH:15][C:16]([CH:19]=[CH:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:2][OH:3])=[O:30])=[O:22])=[CH:17][CH:18]=2)[CH2:8][CH2:7]1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 68407727HCID 68407727, compound

Product 1

HCID 86647576HCID 86647576, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Hydroxylamine hydrochloride (0.63 g, 9 mmol) in methanol (3 mL) was mixed with KOH (0.51 g, 12.3 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-(3-(E)-(4-(3-(cyclopropylamino)-2-(4-fluorophenyl)-3-oxoprop-1-en-1-yl) phenyl)acrylamido)hexenoate (0.24 g, 0.5 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 (1×200 mL). The ethyl acetate layer was washed with water (100 mL), dried over anhydrous Na2SO4 and concentrated to obtain a sticky compound, subsequently triturated with DCM (15 mL), to obtain a solid. The solid obtained was filtered and washed with DCM (5 mL) to afford the title compound (0.075 g, 32% yield). 1H NMR (DMSO-d6) δ (ppm): 0.51 (2H, m, —CH2), 0.62-0.64 (2H, t, —CH2), 1.24 (2H, m, —CH2), 1.40-1.49 (4H, m, —CH2), 1.91-1.93 (2H, d, —CH2), 2.74-2.76 (1H, m, —CH), 3.12-3.13 (2H, d, —CH2) 6.53-6.57 (1H, d, ═CH), 6.99-7.01 (2H, d, Ar—H), 7.18-7.22 (4H, m, Ar—H), 7.27 (1H, s, ═CH), 7.28-7.32 (1H, d, ═CH), 7.37-7.39 (2H, d, Ar—H), 7.82-7.83 (1H, d, —NH), 8.06 (1H, s, —NH), 8.67 (1H, s, —OH), 10.34 (1H, s, —NH). MS m/z: 480.3 (M++1).

Workup

  1. customsonicated for
  2. custom2 minutes and the white precipitate formed
  3. filtrationwas filtered
  4. extractionextracted with ethyl acetate (1×200 mL)
  5. washThe ethyl acetate layer was washed with water (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customto obtain a sticky compound
  9. customsubsequently triturated with DCM (15 mL)
  10. customto obtain a solid
  11. customThe solid obtained
  12. filtrationwas filtered
  13. washwashed with DCM (5 mL)

Sources & evidence

ORD record
ord-9fb68e83a1df40208730fb5ae6345bc2
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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