Acetic Acid → HCID 24993419, compound

HRID 1673227Notes

Reaction equation

HRID 1673227 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[CH:25]([NH:26][C:27](=S)[CH2:28][C:29](=O)[CH3:30])[CH2:24][C:23]([CH3:34])([CH3:33])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.[NH2:35][NH2:36].CC(O)=O>CCO.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[CH:25]([NH:26][C:27]4[CH:28]=[C:29]([CH3:30])[NH:36][N:35]=4)[CH2:24][C:23]([CH3:34])([CH3:33])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 86622719HCID 86622719, compound

Product 1

HCID 24993419HCID 24993419, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of the product of Step B (56 mg, 0.11 mmol), hydrazine (6.6 μL, 0.21 mmol), and AcOH (12.0 μL, 0.21 mmol) in 5.0 mL of EtOH was refluxed for 16 h. The reaction mixture was then cooled to rt, diluted with Et2O (50 mL), and washed with saturated aq NaHCO3 (2×50 mL) and brine (50 mL). After phase separation, the organic phase was dried over MgSO4 and concentrated. Chromatography on a Biotage 40+S cartridge using 2:3 v/v acetone/hexanes as the eluant afforded the title compound: 1H NMR δ 1.48 (s, 3H), 1.54 (s, 3H), 1.82 (t, J=12.4, 1H), 2.26 (s, 3H), 2.41 (dd, J=5.9, 13.3, 1H), 3.86 (br. s, 1H), 4.92 (m, 1H), 5.45 (s, 1H), 7.00 (d, J=8.4, 2H), 7.15-7.26 (m, 5H), 7.97 (s, 1H).

Workup

  1. temperaturewas refluxed for 16 h
  2. washwashed with saturated aq NaHCO3 (2×50 mL) and brine (50 mL)
  3. customAfter phase separation
  4. dry with materialthe organic phase was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-53108e7b6e7340f4852eb673b9bdb6bb
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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