Dichloromethane → HCID 23648838, compound

HRID 404921Notes

Reaction equation

HRID 404921 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[N:19]=[C:18]([CH:20]([N:22]4C(=O)C5C(=CC=CC=5)C4=O)[CH3:21])[O:17][N:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].ClCCl.O.NN>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[N:19]=[C:18]([CH:20]([NH2:22])[CH3:21])[O:17][N:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 69435327HCID 69435327, compound

Product 1

HCID 23648838HCID 23648838, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Example 40C (372 mg) in 9:1 dichloromethane:ethanol (25 mL) was charged with hydrazine hydrate (379 uL) and refluxed for 4 hours. The solvent was dried in vacuum and the reaction mixture was stirred in dichloromethane for 3 hours. The solid was removed by filtration and the residue was concentrated under vacuum to yield 265 mg of the title product. 1H NMR (300 MHz, CDCl3) δ ppm 7.91 (s, 1H) 7.15-7.25 (m, 2H) 6.88-7.00 (m, 2H) 4.46-4.61 (m, 1H) 4.28-4.41 (m, J=6.86 Hz, 1H) 1.58 (d, J=6.99 Hz, 3H) 1.36 (d, J=5.88 Hz, 6H) MS (DCI): m/z 347 (M+H).

Workup

  1. temperaturerefluxed for 4 hours
  2. customThe solvent was dried in vacuum
  3. customThe solid was removed by filtration
  4. concentrationthe residue was concentrated under vacuum

Sources & evidence

ORD record
ord-c798777b1e1f43e19a687763683ac94c
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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