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Acetic Anhydride → n-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)acetamide

HRID 404871
Notes
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Reaction equation

HRID 404871 reaction equation
[CH:1]([O:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([CH:20]([N:22]4C(=O)C5[C:24](=CC=CC=5)[C:23]4=[O:32])[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].O.NN.C(N(CC)CC)C.C(OC(=O)C)(=O)C>ClCCl.CCCCCC.C(OCC)(=O)C.CO.C(O)C>[CH:1]([O:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([CH:20]([NH:22][C:23](=[O:32])[CH3:24])[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 694391172-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)-1h-isoindole-1,3(2h)-dione

Product 1

HCID 23648576n-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)acetamideYield 24.2%

Reagents, catalysts & solvents

5
HCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 3C (200 mg, 0.41 mmol) at room temperature in dichloromethane (5 mL) was added hydrazine hydrate (197 uL, 4.1 mmol). Ethanol was added until a clear, single phase was formed. After an hour at room temperature, the solvent was removed under vacuum and the reaction mixture was thoroughly dried. To the resulting mixture was added dichloromethane (5 mL), triethylamine (300 uL, 2.15 mmol) and acetic anhydride (150 uL, 1.59 mmol). After two hours at room temperature, methanol was added and the solution was stirred for additional hour. The mixture was concentrated and the product was isolated via silica column chromatography (using a gradient of 25 to 75% ethyl acetate in hexane) and yielded 40 mg of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.16-7.23 (m, 3H) 6.83-6.95 (m, 4H) 5.66 (d, J=8.09 Hz, 1H) 5.25-5.43 (m, 1H) 4.52 (heptet, J=6.25 Hz, 1H) 2.00 (s, 3H) 1.57 (d, J=6.99 3 H) 1.35 (d, J=6.25 Hz, 6H), MS (DCI): m/z 403 (M+H).

Workup

  1. customwas formed
  2. waitAfter an hour at room temperature
  3. customthe solvent was removed under vacuum
  4. customthe reaction mixture was thoroughly dried
  5. concentrationThe mixture was concentrated
  6. customthe product was isolated via silica column chromatography (

Sources & evidence

ORD record
ord-e4623637a0c54002b39fb3769ff31b34
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748627B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes