Acetic Acid → HCID 58399171, compound

HRID 641706Notes

Reaction equation

HRID 641706 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:24][N:16]3[C:17]4[C:22]([CH:23]=[C:15]3[CH2:14][CH2:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].CI.[CH3:29]C(O)=O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:29])[CH:12]2[CH2:24][N:16]3[C:17]4[C:22]([CH:23]=[C:15]3[CH2:14][CH2:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58399152HCID 58399152, compound

Product 1

HCID 58399171HCID 58399171, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Step 8 (3 g) in 100 mL of DMF were added 0.4 g of NaH (60% in mineral oil) and 1.2 mL of MeI. After stirring for 1 h at room temperature, 1 mL of AcOH was added and the mixture was concentrated under vacuum and the residue was dissolved in 200 mL of 1:1 hexane/EtOAc and filtered through a pad of silica gel. The filtrate was concentrated and the residue was swished from 2:1 hexane/EtOAc to give 2.5 g of the title product. 1H NMR (500 MHz, acetone-d6) δ 8.10 (m, 2H), 7.47 (m, 3H), 7.28 (d, 1H), 7.09 (dd, 1H), 7.02 (dd, 1H), 6.15 (s, 1H), 4.55 (m, 1H), 4.20 (m, 1H), 3.88 (t, 1H), 3.05-3.12 (m, 1H), 2.92-3.02 (m, 1H), 2.97 (s, 3H), 1.92-2.02 (m, 1H), 1.66 (m, 1H).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in 200 mL of 1:1 hexane/EtOAc
  3. filtrationfiltered through a pad of silica gel
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-64e5d76d4e4547c5b31e60230e4a41dc
Source dataset
uspto-grants-2010_04
Patent number
US07696222B2

Reaction notes

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