Water → HCID 18706797, compound

HRID 1421866Notes

Reaction equation

HRID 1421866 reaction equation
CS[CH:3]1[CH2:12][CH:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH2:10]2)[C:5](=O)[C:4]1=[CH:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.[CH3:28][NH:29][NH2:30].O>C(O)C>[C:24]([O:23][C:21]([N:18]1[CH2:17][CH2:16][N:15]([C:14]2[C:4]3[CH2:3][CH2:12][C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]=3[N:29]([CH3:28])[N:30]=2)[CH2:20][CH2:19]1)=[O:22])([CH3:25])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 6061MethylhydrazineHCID 86755482HCID 86755482, compound

Product 1

HCID 18706797HCID 18706797, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(Methylthio(4-(tert-butyloxycarbonyl)piperazin 1-yl)methylene-4,5-dihydro-2H-naphthalen-1-one (3.2 g, 8.2 mmol) and methylhydrazine (5 ml) were kept in ethanol (30 ml) for four days. Water (150 ml) was added, and the mixture extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine, dried (MgSO4), evaporated in vacuo, and purified by flash chromatography, eluting with hexane:ethyl acetate (4:1 v/v) to give 3-(4-(tert-butyloxycarbonyl)piperazin-1-yl)-4,5-dihydro-1-methyl-1H-benzo[g]indazole (342 mg, 11%) as a colourless oil; 1H NMR (360 MHz, CDCl3) δ 1.52 (9H, s, tBu), 2.67 (2H, t, J=7.3 Hz, CCH2CH2C), 2.94 (2H, t, J=7.3 Hz, CCH2CH2C), 3.15 (4H, t, J=5.1 Hz, NCH2), 3.61 (4H, t, J=5.1 Hz, NCH2), 4.15 (3H, s, Me), 7.22-7.34 (3H, m, ArH), 7.55 (1H, d, J=7.7 Hz, H-9). Iradiation at δ 4.15 gave a positive nOe to the doublet at δ 7.55, and the reverse; and 3-(4-(tert-butyloxycarbonyl)piperazin-1-yl)-4,5-dihydro-2-methyl-2H-benzo[g]indazole (561 mg, 19%) as a white solid δ (360 MHz, CDCl3) 1.54 (9H, s, tBu), 2.86 (2H, t, J=7.8 Hz, CCH2CH2C), 2.95 (2H, t, J=7.8 Hz, CCH2CH2C), 3.08 (4H, t, J=4.9 Hz, NCH2), 3.60 (4H, t, J=4.9 Hz, NCH2), 7.20-7.30 (3H, m, ArH), 7.83 (1H, d, J=7.5 Hz, H-9).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×50 ml)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. custompurified by flash chromatography
  6. washeluting with hexane:ethyl acetate (4:1 v/v)

Sources & evidence

ORD record
ord-ac0f62e8626d40d8b0ed5ba06807d4d9
Source dataset
uspto-grants-2000_06
Patent number
US06080745

Reaction notes

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