Hydrazine hydrate (1:1) → HCID 66835840, compound

HRID 572846Notes

Reaction equation

HRID 572846 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:31][CH:32]1[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]1)[C:11]1[CH:12]=[C:13]([C:17]#[C:18][CH2:19][N:20]2C(=O)C3C(=CC=CC=3)C2=O)[CH:14]=[CH:15][CH:16]=1.O.NN>C(O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:31][CH:32]1[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]1)[C:11]1[CH:12]=[C:13]([C:17]#[C:18][CH2:19][NH2:20])[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66835786HCID 66835786, compound

Product 1

HCID 66835840HCID 66835840, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(3-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]-phenyl}prop-2-ynyl)isoindole-1,3-dione (70 mg) and hydrazine hydrate (70 μL) in ethanol (0.7 mL) is stirred a room temperature for 3 hours. Ethanol is removed under reduced pressure and 1N hydrochloric acid in water is added to the organic residue and stirred for 5 minutes. The mixture is filtered, cake washed with ethyl acetate. The filtrate is extracted by dichloromethane. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure The residue purified by chromatography (dichloromethane/methanol/ammonia from 90/10/1) to afford 3-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]phenyl}prop-2-ynylamine melting at 101° C.

Workup

  1. customEthanol is removed under reduced pressure and 1N hydrochloric acid in water
  2. additionis added to the organic residue
  3. filtrationThe mixture is filtered
  4. washcake washed with ethyl acetate
  5. extractionThe filtrate is extracted by dichloromethane
  6. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure The residue
  8. custompurified by chromatography (dichloromethane/methanol/ammonia from 90/10/1)

Sources & evidence

ORD record
ord-f899204e302645b3b7427f76c9ba776b
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

Loading…