Dimethylformamide → HCID 21255055, compound

HRID 636387Notes

Reaction equation

HRID 636387 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12]C[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]1([S:20]([C:23]2[C:24]([S:34][CH3:35])=[N:25][N:26]3[C:31](Cl)=[CH:30][C:29]([CH3:33])=[N:28][C:27]=23)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C[N:37](C=O)C>>[C:14]1([S:20]([C:23]2[C:24]([S:34][CH3:35])=[N:25][N:26]3[C:31]([N:37]4[CH2:10][CH2:9][N:8]([CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[CH2:13][CH2:12]4)=[CH:30][C:29]([CH3:33])=[N:28][C:27]=23)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 761901-BenzylpiperidineHCID 109810973-Benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 21255055HCID 21255055, compoundYield 73%

Procedure

0.35 g (2 mmol) of N-benzyl-piperidine was added to a solution of 0.35 g (1 mmol) of 3-benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine in 5 ml of DMF and stirred at 60° for 2 hrs. The reaction solution was cooled to RT and evaporated in a high vacuum. The residue was partitioned between 2N NaOH and CH2Cl2. The aqueous phase was extracted three times with CH2Cl2, and the combined organic phases were dried (MgSO4), filtered and evaporated. Subsequent chromatography (SiO2, CH2Cl2/MeOH 19:1) and crystallization from EtOH yielded 0.36 g (73%) of 3-benzenesulphonyl-7-(4-benzyl-piperazin-1-yl)-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine as colorless crystals m.p. 156-158°.

Workup

  1. customevaporated in a high vacuum
  2. customThe residue was partitioned between 2N NaOH and CH2Cl2
  3. extractionThe aqueous phase was extracted three times with CH2Cl2
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customSubsequent chromatography (SiO2, CH2Cl2/MeOH 19:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-a7f6a8dfeff94e57a82ca8fd1fda09d0
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

Loading…