Hydrochloric Acid → HCID 67418262, compound

HRID 1429355Notes

Reaction equation

HRID 1429355 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH:13]([N:21]([CH2:33][C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36]([OH:38])=[O:37])[S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32])(=[O:24])=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.NN.Cl>C(O)C>[NH2:3][CH2:12][CH:13]([N:21]([CH2:33][C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36]([OH:38])=[O:37])[S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32])(=[O:24])=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 67419089HCID 67419089, compound

Product 1

HCID 67418262HCID 67418262, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of compound 2e (100 mg, 0.17 mmol) and hydrazine monohydrate 98% (85 mg, 1.7 mmol) in ethanol (5 mL) was heated to reflux for 2 hr. The reaction mixture was cooled down to rt and acidified to pH=3 with 1N aqueous HCl. The precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by prep-HPLC to give compound 2f as a white solid (30 mg, 39% yield).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hr
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-f06993c136b445bf86667d007d8d4fcd
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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