Triethylamine → HCID 22004611, compound

HRID 324370Notes

Reaction equation

HRID 324370 reaction equation
[CH2:1]([N:8]([C:13]1[N:18]=[C:17]([CH3:19])[N:16]=[C:15]2[N:20]([C:25]3[C:30]([Cl:31])=[CH:29][C:28]([Cl:32])=[CH:27][C:26]=3[Cl:33])[N:21]=[C:22]([S:23][CH3:24])[C:14]=12)[CH2:9][CH2:10][CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][C:35](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:36].C(N(CC)CC)C>C(Cl)Cl>[C:35]([O:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:13]1[N:18]=[C:17]([CH3:19])[N:16]=[C:15]2[N:20]([C:25]3[C:30]([Cl:31])=[CH:29][C:28]([Cl:32])=[CH:27][C:26]=3[Cl:33])[N:21]=[C:22]([S:23][CH3:24])[C:14]=12)(=[O:36])[CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 22004591HCID 22004591, compound

Product 1

HCID 22004611HCID 22004611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-{benzyl-[6-methyl-3-methylsulfanyl-1-(2,4,6-trichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]amino}-propanol (80 mg, 0.148 mmol) in 1 ml of methylene chloride was treated with acetic anhydrous (38 mg, 0.37 mmol) and triethyl amine (38 mg, 0.37 mmol) and stirred at room temperature for 15 hours. The mixture was quenched with water and a few drops of dilute HCl and extracted with ethyl acetate. The organic layer was neutralized with aqueous sodium bicarbonate and washed with brine, separated, dried and concentrated to give the title compound as an oil. The oil was purified through silica gel column chromatography using chloroform as eluent to give 57 mg of the title compound as a white glass form. 1H NMR (CDCl3): 2.0(s,3H, 2.03(m,2H), 2.45(s,3H), 2.60(s,3H), 3.74(t,2H), 4.10(t,2H), 5.1(s,2H), 7.2-7.4(m,5H), 7.50(s,2H) ppm.

Workup

  1. customThe mixture was quenched with water and a few drops of dilute HCl
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. customseparated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e5aff774fbef4629ac9e92e91bfe9088
Source dataset
uspto-grants-2001_04
Patent number
US06218397B1

Reaction notes

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