Isopropyl iodide → HCID 14424032, compound

HRID 620176Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[S:17][C:13]=2[N:12]2[C:27]([CH3:30])=[N:28][N:29]=[C:11]2[CH2:10][N:9]=1.[OH-].[K+].[CH:33](I)([CH3:35])[CH3:34]>COCCO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH:33]([CH3:35])[CH3:34])=[CH:22][CH:21]=3)[S:17][C:13]=2[N:12]2[C:27]([CH3:30])=[N:28][N:29]=[C:11]2[CH2:10][N:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 0.5 g of thienotriazolodiazepine compound obtained in Example 5, 0.2 g of potassium hydroxide and 0.62 g of isopropyl iodide in 20 ml of 2-methoxyethanol is stirred at 90° C. for 4 hours, and then the resulting mixture is concentrated to dryness. The residue is dissolved in 50 ml of chloroform, washed with water and dried over anhydrous magnesium sulfate. After separating by filtration, the filtrate is concentrated under reduced pressure and the residue is crystallized from isopropyl ether-ethyl acetate to give 0.3 g of 4-(2-chlorophenyl)-2-[2-(4-isopropoxyphenyl)ethyl]-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine as colorless crystals, melting at 121°-124° C.

Workup

concentrationthe resulting mixture is concentrated to dryness
dissolutionThe residue is dissolved in 50 ml of chloroform
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
customAfter separating by filtration
concentrationthe filtrate is concentrated under reduced pressure
customthe residue is crystallized from isopropyl ether-ethyl acetate

Sources & evidence

ORD record: ord-846f54c61bda4fa49581cbedace52387
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04820703

Reaction notes

Loading…