Hydrazine hydrate (1:1) → HCID 77014396, compound

HRID 474453Notes

Reaction equation

HRID 474453 reaction equation
FC(F)(F)C(O)=O.O=C1C2C(=CC=CC=2)C(=O)[N:10]1[CH2:19][C:20]1[S:24][C:23]([NH:25][C:26]2[CH:27]=[C:28]([CH:44]=[CH:45][CH:46]=2)[CH2:29][NH:30][C:31]2[C:40]3[C:35](=[C:36]([C:41]([NH2:43])=[O:42])[CH:37]=[CH:38][CH:39]=3)[N:34]=[CH:33][N:32]=2)=[N:22][CH:21]=1.O.NN>C(O)C>[NH2:10][CH2:19][C:20]1[S:24][C:23]([NH:25][C:26]2[CH:27]=[C:28]([CH:44]=[CH:45][CH:46]=2)[CH2:29][NH:30][C:31]2[C:40]3[C:35](=[C:36]([C:41]([NH2:43])=[O:42])[CH:37]=[CH:38][CH:39]=3)[N:34]=[CH:33][N:32]=2)=[N:22][CH:21]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 86662389HCID 86662389, compound

Product 1

HCID 77014396HCID 77014396, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

24 mg (0.04 mmol) 4-{3-[5-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-thiazol-2-ylamino]-benzylamino}-quinazoline-8-carboxylic acid amide trifluoroacetic acid salt were dissolved in 1 ml ethanol and treated with 10 μl (0.21 mmol) hydrazine hydrate. The mixture was stirred overnight at 50° C. in a closed vessel. Additional 40 μl hydrazine hydrate were added and the mixture was stirred at 60° C. for 24 h. The reaction mixture was evaporated and the crude product was purified using preparative HPLC. The product was treated with HCl in methanol and concentrated in the SpeedVac.

Workup

  1. stirringthe mixture was stirred at 60° C. for 24 h
  2. customThe reaction mixture was evaporated
  3. customthe crude product was purified
  4. additionThe product was treated with HCl in methanol
  5. concentrationconcentrated in the SpeedVac

Sources & evidence

ORD record
ord-c469d8f44d0847679f310f22a10892c4
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Reaction notes

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