Hydrazine → HCID 178427630, compound

HRID 234824

Reaction equation

HRID 234824 reaction equation
C(OC(NCCCl)=O)(C)(C)C.[NH2:12][NH2:13].F[C:15]1[C:28]2[C:27](=O)[C:26]3[CH:25]=[N:24][CH:23]=[CH:22][C:21]=3[C:20](=[O:30])[C:19]=2[C:18]([O:31][S:32]([C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=2)(=[O:34])=[O:33])=[CH:17][CH:16]=1.ClC1C2C(=O)C3C=NC=CC=3C(=O)C=2C(OS(C2C=CC(C)=CC=2)(=O)=O)=CC=1.C(N(CC)C(C)C)(C)C>C1COCC1>[C:38]1([CH3:41])[CH:39]=[CH:40][C:35]([S:32]([O:31][C:18]2[CH:17]=[CH:16][C:15]3[NH:13][N:12]=[C:27]4[C:26]5[CH:25]=[N:24][CH:23]=[CH:22][C:21]=5[C:20](=[O:30])[C:19]=2[C:28]=34)(=[O:33])=[O:34])=[CH:36][CH:37]=1

Participants

7

Reactant 5

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 3795708N-Boc-2-chloroethylamineHCID 105728809-Fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dioneHCID 199747549-Chloro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione

Product 1

HCID 178427630HCID 178427630, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(2-N-tert-butoxycarbonylaminoethyl)hydrazine is prepared by reaction of N-t-butoxycarbonyl-2-chloro-ethylamine with hydrazine following a procedure adapted from J. Med. Chem. 7, 493, (1964). Under a nitrogen atmosphere a solution of (2-N-tert-butoxycarbonylaminoethyl)hydrazine (9.2 g) in anhydrous THF (10 mL) is added during 30' to the stirred 9:1 mixture of 9-fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione and 9-chloro-6-(p-toluenesulfonyloxy)benzo [g]isoquinoline-5,10-dione of Preparative Example 15b (3.0 g) in THF (25 mL) containing N,N-diisopropylethylamine (1.38 mL). A slightly exothermic reaction ensues, and the reaction temperature increases from 21° C. to 24° C. After stirring for one hour at room temperature the obtained precipitate is recovered by suction, washed with THF/n-hexane 1/1 (15 mL) and dried at 40° C. under vacuum, to give 2-[2-(N-tert-butoxycarbonylamino)ethyl[-5-(p-toluenesulfonyloxy)iso-quino[8,7,6-cd]indazole-6(2H)-one (1.33 g).

Workup

  1. customA slightly exothermic reaction
  2. temperaturethe reaction temperature increases from 21° C. to 24° C
  3. stirringAfter stirring for one hour at room temperature the obtained precipitate
  4. customis recovered by suction
  5. washwashed with THF/n-hexane 1/1 (15 mL)
  6. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-d8fd736de86e4c2b8e3db1257e6b8df0
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Linked notes

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