Sodium Hydroxide → HCID 57474455, compound

HRID 552932Notes

Reaction equation

HRID 552932 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([NH:20]C(=O)C4C=CC=CC=4)=[S:19])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.[OH-].[Na+]>C1COCC1>[CH3:1][N:2]1[CH2:3][CH:4]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([NH2:20])=[S:19])[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15951266HCID 15951266, compound

Product 1

HCID 57474455HCID 57474455, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 63 (1.12 g, 2.868 mmol) in THF (20 mL) was treated with 2 N NaOH (3.1 mL, 6.309 mmol) at room temperature and the resulting solution was refluxed for 5 h. The reaction was brought to room temperature, solvent was evaporated. The crude was diluted with water (20 mL) and ethyl acetate (20 mL). The precipitated solid was filtered, washed with water (10 mL), EtOAc (10 mL) and ether (2×10 mL) and dried under vacuum to obtain compound 65 (0.65 g, 79%). mp 209-211° C.: 1H NMR (DMSO-d6) δ 2.27 (s, 3H), 2.50-2.56 (m, 4H), 3.00-3.08 (m, 2H), 6.05 (s, 1H), 6.98 (d, 1H, J=8.4 Hz), 7.32-7.40 (m, 3H), 7.67 (s, 1H), 9.51 (s, 1H), 11.15 (s, 1H); ESI-MS m/z (%):: 287 (M+, 71), 249 (46), 244 (100).

Workup

  1. temperaturethe resulting solution was refluxed for 5 h
  2. customwas brought to room temperature
  3. customsolvent was evaporated
  4. additionThe crude was diluted with water (20 mL) and ethyl acetate (20 mL)
  5. filtrationThe precipitated solid was filtered
  6. washwashed with water (10 mL), EtOAc (10 mL) and ether (2×10 mL)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e445eb7d4ab544dca6396a564b2b7c16
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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