Hydrazine hydrate (1:1) → HCID 44514152, compound

HRID 1011636Notes

Reaction equation

HRID 1011636 reaction equation
[CH2:1]([C:5]1([N:43]([CH3:45])[CH3:44])[CH2:10][CH2:9][C:8]([C:21]2[NH:22][C:23]3[C:28]([C:29]=2[CH2:30][CH2:31][N:32]2C(=O)C4C(=CC=CC=4)C2=O)=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH3:20])=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].O.NN>CO.[OH-].[Na+]>[NH2:32][CH2:31][CH2:30][C:29]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][C:21]=1[C:8]1([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH3:20])=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][CH2:10][C:5]([N:43]([CH3:45])[CH3:44])([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 44514150HCID 44514150, compound

Product 1

HCID 44514152HCID 44514152, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-(2-(2-(4-butyl-4-(dimethylamino)-1-(3-methyl-1H-indol-2-yl)cyclohexyl)-1H-indol-3-yl)ethyl)isoindolin-1,3-dione (450 mg, 0.749 mmol) and hydrazine monohydrate (2 ml, 41.2 mmol) were dissolved in methanol (20 ml) and then boiled with reflux for 45 min. For work up the batch was diluted with 1N NaOH (50 ml) and extracted with diethyl ether (3×20 ml). The combined organic phases were dried over Na2SO4 and then concentrated until dry. The product was obtained as a light beige-coloured solid with a yield of 302 mg (86%, melting point 105-112° C.). According to the NMR spectrum it was a mixture of the two possible diastereoisomers in a ratio of approx. 30:70.

Workup

  1. temperaturewith reflux for 45 min
  2. extractionextracted with diethyl ether (3×20 ml)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated
  5. customuntil dry
  6. customThe product was obtained as a light beige-coloured solid with a yield of 302 mg (86%, melting point 105-112° C.)
  7. additiona mixture of the two possible diastereoisomers in a ratio of approx. 30:70

Sources & evidence

ORD record
ord-4ac12c367f3841f88e801770f21a2fb1
Source dataset
uspto-grants-2011_07
Patent number
US07977370B2

Reaction notes

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