Hydrazine hydrate (1:1) → HCID 136385274, compound

HRID 1467533Notes

Reaction equation

HRID 1467533 reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([C:14]2[CH:15]=[C:16]([CH:20]3[CH:29]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([N:38]5[CH2:43][CH2:42][N:41]([C:44](=[O:48])[CH:45]([CH3:47])[CH3:46])[CH2:40][CH2:39]5)=[O:37])[CH:31]=4)[C:28](=O)[C:27]4[C:26]([C:50](OC)=[O:51])=[CH:25][CH:24]=[CH:23][C:22]=4[NH:21]3)[CH:17]=[CH:18][CH:19]=2)=[O:13])[CH2:8][CH2:7]1)(=O)[CH:2]([CH3:4])[CH3:3].[OH2:54].[NH2:55][NH2:56]>CO>[C:1]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([C:14]2[CH:15]=[C:16]([CH:20]3[NH:21][C:22]4[C:27]5[C:28](=[N:55][NH:56][C:50](=[O:51])[C:26]=5[CH:25]=[CH:24][CH:23]=4)[CH:29]3[C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([N:38]4[CH2:43][CH2:42][N:41]([C:44](=[O:48])[CH:45]([CH3:47])[CH3:46])[CH2:40][CH2:39]4)=[O:37])[CH:31]=3)[CH:17]=[CH:18][CH:19]=2)=[O:13])[CH2:8][CH2:7]1)(=[O:54])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67259126HCID 67259126, compound

Product 1

HCID 136385274HCID 136385274, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 2,3-bis(3-(4-isobutyrylpiperazine-1-carbonyl)phenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (90 mg, 0.12 mmol) in hydrazine monohydrate (5 mL) and methanol (2 mL) was stirred at 25° C. for 4 hr. The mixture was extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by prep-HPLC to give 8,9-bis(3-(4-isobutyrylpiperazine-1-carbonyl)phenyl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (3.2 mg, yield: 4%) as a white solid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (50 mL×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto give crude product
  6. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-7441fce66cad45f585ab2a33e869e624
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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