Tetrahydrofuran → HCID 178456822, compound

HRID 616759Notes

Reaction equation

HRID 616759 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:18]([CH3:19])=[N:17][N:16]([CH3:20])[C:10]=2[N:11]=[C:12](S)[CH2:13][N:14]=1.O1CCCC1.[CH2:26]([NH2:29])[C:27]#[CH:28]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:18]([CH3:19])=[N:17][N:16]([CH3:20])[C:10]=2[N:11]=[C:12]([NH:29][CH2:26][C:27]#[CH:28])[CH2:13][N:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 239041PropargylamineHCID 178433926HCID 178433926, compound

Product 1

HCID 178456822HCID 178456822, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4.65 g. of 4-(2-chlorophenyl)-1,6-dihydro-1,3-dimethylpyrazolo[3,4-e][1,4]diazepine-7-thiol (prepared as disclosed in U.S. Pat. No. 3,770,762), 250 ml. of tetrahydrofuran, 3.0 g. of 2-propynylamine and 20 ml. of methanol is allowed to stand at room temperature (20°-30° C.) for 3 days, then evaporated at reduced pressure to give a residue of 4-(2-chlorophenyl-1,6-dihydro-1,3-dimethyl-7-(2-propynylamino)pyrazolo[3,4-e][1,4]diazepine; m.p. 165°-167° C. after crystallization from acetonitrile. For further purification, the product is dissolved in 9:1 tolueneacetonitrile and chromatographed on a column of neutral alumina. The column is eluted with 9:1 methanol-acetonitrile and the eluate is evaporated at reduced pressure to give a residue of m.p. 176°-178° C. (dec.).

Workup

  1. additionA mixture of 4.65 g
  2. customto stand at room temperature
  3. custom(20°-30° C.)
  4. customfor 3 days
  5. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-2721be956da24a0fb128d82fff0f8841
Source dataset
uspto-grants-1978_02
Patent number
US04075408

Reaction notes

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