Sodium hydride → HCID 68445623, compound

HRID 1163425Notes

Reaction equation

HRID 1163425 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:5]([N+:36]([O-:38])=[O:37])=[CH:6][C:7]([C:20](=[O:35])[NH:21][C:22]2[CH:30]=[C:29]3[C:25]([CH:26]=[N:27][N:28]3[S:31]([CH3:34])(=[O:33])=[O:32])=[CH:24][CH:23]=2)=[C:8](CCNCCOS(C)(=O)=O)[CH:9]=1>C1COCC1>[NH2:3][C:4]1[C:5]([N+:36]([O-:38])=[O:37])=[CH:6][C:7]2[C:20](=[O:35])[N:21]([C:22]3[CH:30]=[C:29]4[C:25]([CH:26]=[N:27][N:28]4[S:31]([CH3:34])(=[O:33])=[O:32])=[CH:24][CH:23]=3)[CH2:7][CH2:20][N:21]([CH2:22][CH3:23])[C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86615224HCID 86615224, compound

Product 1

HCID 68445623HCID 68445623, compoundYield 192.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (60%, 266 mg, 6.7 mol) was added to a solution of crude methanesulfonic acid 2-{[5-amino-2-(1-methanesulfonyl-1H-indazol-6-ylcarbamoyl)-4-nitrophenyl]ethylamino}ethyl ester (2.6 mmol) in THF (10 mL) at room temperature. The solution was stirred at reflux for 3 h. The solvent was removed under reduced pressure, and the residue was taken up in EtOAc and washed with water (10 mL). The organic layer was separated, dried over MgSO4, and the solvent was removed under reduced pressure to afford 8-amino-1-ethyl-4-(1-methanesulfonyl-1H-indazol-6-yl)-7-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (1.1 g, 2.5 mmol).

Workup

  1. temperatureat reflux for 3 h
  2. customThe solvent was removed under reduced pressure
  3. washwashed with water (10 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4ad716565aff4c2fb72cd3bbe420adc1
Source dataset
uspto-grants-2010_10
Patent number
US07820821B2

Reaction notes

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