Methylamine → HCID 19704991, compound

HRID 727278Notes

Reaction equation

[CH:1]1([C:7]2[C:13]3[C:14]([CH3:18])=[C:15]([CH3:17])[S:16][C:12]=3[N:11]3[C:19]([CH3:22])=[N:20][N:21]=[C:10]3[CH:9]([CH2:23][C:24]([OH:26])=O)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:27]([N:29](CC)CC)C.C(Cl)(=O)C(C)(C)C.CN>O.O1CCCC1.CN(C)C=O>[CH3:27][NH:29][C:24](=[O:26])[CH2:23][CH:9]1[N:8]=[C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:13]2[C:14]([CH3:18])=[C:15]([CH3:17])[S:16][C:12]=2[N:11]2[C:19]([CH3:22])=[N:20][N:21]=[C:10]12

Participants

Conditions

Temperature: -5 °C

Procedure

(±)-4-Cyclohexyl-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid (0.54 g) and triethylamine (0.22 ml) are added to a mixed solvent of dimethylformamide (20 ml) and tetrahydrofuran (10 ml). The mixture is cooled to -5° C. and pivaloyl chloride (0.18 ml) is dropwise added at said temperature. Ten minutes later, a 40% aqueous solution (2 ml) of methylamine is dropwise added at said temperature and the mixture is stirred at room temperature for 2 hours. Water is added to the reaction mixture, and the mixture is extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The solvent is distilled away under reduced pressure and the residue is recrystallized from ethyl acetate to give (±)-N-methyl-4-cyclohexyl-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide, melting point 228°-231° C.

Workup

extractionthe mixture is extracted with ethyl acetate
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent is distilled away under reduced pressure
customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-fe8c639e6acc466597f5ab3d83498104
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712274

Reaction notes

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