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Sodium Bisulfite → HCID 178429876, compound

HRID 1047571
Notes
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Reaction equation

HRID 1047571 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[N:8]=[C:7]2[CH:19]=O)([O-:3])=[O:2].[CH3:21][CH:22]1[CH2:27][N:26]([C:28]2[CH:29]=[C:30]([NH2:35])[C:31]([NH2:34])=[CH:32][CH:33]=2)[CH2:25][CH2:24][O:23]1.S(=O)(O)[O-].[Na+]>C1COCC1.Cl.C(OCC)(=O)C>[CH3:21][CH:22]1[O:23][CH2:24][CH2:25][N:26]([C:28]2[CH:33]=[CH:32][C:31]3[NH:34][C:19]([C:7]4[C:6]5[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=5)[N:9]([CH:13]5[CH2:18][CH2:17][CH2:16][CH2:15][O:14]5)[N:8]=4)=[N:35][C:30]=3[CH:29]=2)[CH2:27]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 23665763Sodium BisulfiteHCID 683850274-(2-Methylmorpholino)benzene-1,2-diamineHCID 866732115-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde

Product 1

HCID 178429876HCID 178429876, compoundYield 55.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric Acid
Catalyst
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

5-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde (150 mg, 0.545 mmol) and 4-(2-methylmorpholino)benzene-1,2-diamine (113 mg, 0.545 mmol) were dissolved in THF (10 mL) and 2N HCl (1 drop) was added. The solution was heated at a gentle reflux for 30 min. Then, 1N sodium bisulfite (104 mg, 1 mmol; 2 mL of a 1N solution) was added and heated at reflux (70° C.) overnight. The solution was cooled to room temperature, and diluted with ethyl acetate (40 mL). The mixture was washed with water and brine, dried over Na2SO4, and concentrated. Purification by flash chromatography (5% CH3OH/CH2Cl2) afforded the title compound (140 mg). 1H NMR: (400 MHz, CDCl3): δ 9.56 (d, 1H, J=1.6 Hz), 8.28 (m, 1H), 7.74 (d, 1H, J=8.8 Hz), 7.64 (m, 1H), 7.36 (m, 1H), 7.03-6.96 (m, 1H), 5.75 (dd, 1H, J=2.8 and 6.4 Hz), 3.99 (m, 2H), 3.79 (m, 3H), 3.38 (m, 2H), 2.84 (m, 1H), 2.51 (m, 2H), 2.11 (m, 2H), 1.86 (m, 1H), 1.74 (m, 2H), 1.22 (d, 3H, J=6.4 Hz).

Workup

  1. temperatureThe solution was heated at
  2. temperaturea gentle reflux for 30 min
  3. temperatureheated
  4. temperatureThe solution was cooled to room temperature
  5. washThe mixture was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customPurification by flash chromatography (5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-328a7e4ea1074e7eb8da8750dcb862c4
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08569511B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes