HCID 18419580, compound → HCID 178424092, compound

HRID 990089Notes

Reaction equation

HRID 990089 reaction equation
[NH2:1][C:2]1[C:35]([NH2:36])=[CH:34][CH:33]=[CH:32][C:3]=1[O:4][CH2:5][CH:6]([OH:31])[CH2:7][NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][CH2:18][C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)[N:20]=2)=[CH:13][CH:12]=1.[N:37]([O-])=O.[Na+]>C(O)(=O)C.O>[NH:36]1[C:35]2[CH:34]=[CH:33][CH:32]=[C:3]([O:4][CH2:5][C@@H:6]([OH:31])[CH2:7][NH:8][CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([S:17][CH2:18][C:19]4[O:23][N:22]=[C:21]([C:24]5[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=5)[N:20]=4)=[CH:13][CH:12]=3)[C:2]=2[N:1]=[N:37]1

Participants

5

Reactant 2

HCID 18419580HCID 18419580, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178424092HCID 178424092, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(2,3-diaminophenoxy)-3-[[2-[4-[[[3-(4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl]thio]phenyl]ethyl]amino]-2-propanol (0.077 g, 0.172 mmol.) in acetic acid (1.2 mL) at 5° C. was added a solution of sodium nitrite (0.013 g, 0.189 mmol) in water (0.5 mL). The mixture was stirred for 30 minutes and evaporated to dryness. The residue was purified by flash chromatography (silica gel; CH2Cl2/MeOH (3/1) to afford 0.079 g of the pure title compound. MP=110° C.

Workup

  1. customevaporated to dryness
  2. customThe residue was purified by flash chromatography (silica gel

Sources & evidence

ORD record
ord-f0af94b8351b45a3998d783338e93da7
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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