Hydrazine hydrate (1:1) → HCID 178487821, compound

HRID 1422951Notes

Reaction equation

HRID 1422951 reaction equation
O.NN.[CH3:4][O:5][C:6]1[N:7]=[C:8]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][C:14]1[NH:13][C:12](=[O:20])[CH:11]([C@H:21]3[CH2:26][CH2:25][C@H:24]([N:27]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:23][CH2:22]3)[O:10][C:9]2=1>ClCCl.CO>[NH2:27][C@H:24]1[CH2:25][CH2:26][C@H:21]([CH:11]2[O:10][C:9]3[C:8]4[C:17](=[CH:18][CH:19]=[C:6]([O:5][CH3:4])[N:7]=4)[N:16]=[CH:15][C:14]=3[NH:13][C:12]2=[O:20])[CH2:22][CH2:23]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178487817HCID 178487817, compound

Product 1

HCID 178487821HCID 178487821, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Hydrazine hydrate (2M solution in methanol, 10 mL, 20.0 mmol, 7.96 eq) is added at room temperature to a stirred solution of 2-[trans-4-(6-methoxy-2-oxo-2,3-dihydro-1H-4-oxa-1,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-isoindole-1,3-dione (1.15 g, 2.51 mmol, 1.0 eq) in dichloromethane (15 mL) and methanol (15 mL). After 16 hours stirring at room temperature and 2 hours stirring at 55° C., solvent is removed and the residue is purified by preparative HPLC to afford 3-(trans-4-amino-cyclohexyl)-6-methoxy-1H-4-oxa-1,5,9-triaza-phenanthren-2-one as a yellow solid (260 mg, 32% yield).

Workup

  1. stirringstirring at 55° C.
  2. customsolvent is removed
  3. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-aefa6a0de1684d7eab940ca768cbd3d7
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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