Methylhydrazine → N,N-dicyclopropyl-7-[(1,5-dimethyl-1,2,4-triazol-3-yl)amino]-10-ethyl-3-methyl-3,5,8,10-tetrazatricyclo[7.3.0.02,6]dodeca-1,4,6,8,11-pentaene-11-carboxamide

HRID 220414Notes

Reaction equation

[C:1]([NH:4][C:5](=S)[NH:6][C:7]1[N:12]=[C:11]2[N:13]([CH2:25][CH3:26])[C:14]([C:16]([N:18]([CH:22]3[CH2:24][CH2:23]3)[CH:19]3[CH2:21][CH2:20]3)=[O:17])=[CH:15][C:10]2=[C:9]2[N:27]([CH3:30])[CH:28]=[N:29][C:8]=12)(=O)[CH3:2].[CH3:32][NH:33][NH2:34]>C(O)(=O)C>[CH:19]1([N:18]([CH:22]2[CH2:23][CH2:24]2)[C:16]([C:14]2[N:13]([CH2:25][CH3:26])[C:11]3=[N:12][C:7]([NH:6][C:5]4[N:4]=[C:1]([CH3:2])[N:33]([CH3:32])[N:34]=4)=[C:8]4[N:29]=[CH:28][N:27]([CH3:30])[C:9]4=[C:10]3[CH:15]=2)=[O:17])[CH2:20][CH2:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(3-acetylthioureido)-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 125A, 17 mg, 0.039 mmol) and methylhydrazine (2.486 μL, 0.046 mmol) in acetic acid (0.5 mL) was heated at 80° C. for 4 h, LC/MS showed starting material still remaining. Additional methylhydrazine (2.486 μL, 0.046 mmol) was added and heating continued for another 2 h, reaction complete. Solvent was evaporated and the crude was purified by preparative HPLC to furnish N,N-dicyclopropyl-4-(1,5-dimethyl-1H-1,2,4-triazol-3-ylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (5.2 mg, 30.7% yield) as an off-white solid.

Workup

temperatureheating
customreaction complete
customSolvent was evaporated
customthe crude was purified by preparative HPLC

Sources & evidence

ORD record: ord-2cbc0d9531e143a8a16da7a43c97bfb5
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202881B2

Reaction notes

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