Pyridine → HCID 86739687, compound

HRID 1632535Notes

Reaction equation

HRID 1632535 reaction equation
Cl([O:3][C:4](=[O:12])[CH2:5][CH2:6][C:7]([O:9]Cl=O)=[O:8])=O.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:19][N:20]1[C:24]([NH:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)[CH:31]=2)=[N:23][C:22]([CH2:43]O)=[N:21]1.[C:45](=[O:48])([O-])[O-].[Na+].[Na+]>O>[CH3:19][N:20]1[C:24]([NH:25][CH2:26][CH2:27][CH2:28][O:48][C:45]2[CH:35]=[CH:30][CH:31]=[C:32]([CH2:36][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH:33]=2)=[N:23][C:22]([CH2:43][O:3][C:4](=[O:12])[CH2:5][CH2:6][C:7]([O:9][CH2:43][C:22]2[N:23]=[C:24]([NH:25][CH2:26][CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][N:37]4[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]4)[CH:31]=3)[N:20]([CH3:19])[N:21]=2)=[O:8])=[N:21]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 55473LoxtidineHCID 86739688HCID 86739688, compound

Product 1

HCID 86739687HCID 86739687, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of butanedioyl dichlorite (0.19 g) and pyridine (3 ml) was added portionwise 1-methyl-5-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-1H-1,2,4-triazole-3-methanol (0.8 g). After stirring at room temperature for 16.5 h, water (10 ml) and anhydrous sodium carbonate (1 g) were added and the solution evaporated to dryness with the aid of ethanol (3×10 ml). To the residue was added ethyl acetate (60 ml), excess anhydrous sodium carbonate and decolourising charcoal. After 2 h, the mixture was filtered, the residue washed with hot ethyl acetate (4×15 ml) and the filtrate evaporated to give a white residue. This was crystallised from ethyl acetate to give the title compound (0.3 g), m.p. 116°-118°.

Workup

  1. customthe solution evaporated to dryness with the aid of ethanol (3×10 ml)
  2. additionTo the residue was added ethyl acetate (60 ml), excess anhydrous sodium carbonate
  3. waitAfter 2 h
  4. filtrationthe mixture was filtered
  5. washthe residue washed with hot ethyl acetate (4×15 ml)
  6. customthe filtrate evaporated
  7. customto give a white residue
  8. customThis was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-893b324510594b0292d069601c0cd1b7
Source dataset
uspto-grants-1984_10
Patent number
US04476126

Reaction notes

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