Hydrazine hydrate (1:1) → HCID 66665520, compound

HRID 872349Notes

Reaction equation

HRID 872349 reaction equation
[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[N:19]=[C:18]([O:20][CH2:21][CH2:22][N:23]5C(=O)C6C(=CC=CC=6)C5=O)[CH:17]=[CH:16][N:15]4[C:34]=3[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.O.NN>C(O)C.C(OC(C)C)(C)C>[NH2:23][CH2:22][CH2:21][O:20][C:18]1[CH:17]=[CH:16][N:15]2[C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([C:2]4([NH2:1])[CH2:5][CH2:4][CH2:3]4)=[CH:7][CH:8]=3)[N:13]=[C:14]2[N:19]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66665331HCID 66665331, compound

Product 1

HCID 66665520HCID 66665520, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

2-(2-{2-[4-(1-Amino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyrimidin-7-yloxy}-ethyl)-isoindole-1,3-dione (340 mg from Step 1) was dissolved in ethanol (6.8 mL), treated with hydrazine hydrate (98%, 0.045 mL) and heated at 80° C. for 22 h. On cooling, the reaction mixture was diluted with diisopropyl ether and filtered. The filtrate was concentrated in vacuo to give the title compound (225 mg).

Workup

  1. temperatureOn cooling
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c8c540af22cb49ac94d039067c527aa9
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

Loading…