Sodium Hydroxide → HCID 57474455, compound

HRID 2043500Notes

Reaction equation

HRID 2043500 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-c43b7872c4ec4e3b9df7e78f5432988b
Source dataset
uspto-grants-2013_11
Patent number
US08586620B2

Reaction notes

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