Diisopropylethylamine → HCID 57691296, compound

HRID 40291Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=O)=[CH:8][CH:7]=2.CCN(C(C)C)C(C)C.[C:28]1([C:34]2[N:39]=[N:38][C:37]([NH:40][NH2:41])=[CH:36][CH:35]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:13]([CH3:18])([CH3:17])[C:14]([NH:41][NH:40][C:37]1[N:38]=[N:39][C:34]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:35][CH:36]=1)=[O:16])=[CH:8][CH:7]=2

Participants

Conditions

Temperature: 23 °C

Procedure

A suspension of 2-(3-methoxyquinolin-6-yl)-2-methylpropanoic acid (92 mg, 375 μmol), DIEA (66 μl, 375 μmol), and o-(7-azabenzotriazol-1-yl)-n,n,n′,n-tetramethyl uronium hexafluorophosphate (143 mg, 375 μmol) in DMF was stirred for 2 h at 23° C. To the solution was added 1-(6-phenylpyridazin-3-yl)hydrazine (70 mg, 375 μmol) and stirred for 72 h at 23° C. Reaction partitioned between 9:1 CHCl3/IPA (25 mL) and 1M NaOH (5 mL). Organic dried over MgSO4 the concentrated to a solid from toluene under reduced pressure. Solid triturated with ACN (2 mL) and collected by filtration. 2-(3-methoxyquinolin-6-yl)-2-methyl-N′-(6-phenylpyridazin-3-yl)propanehydrazide isolated as a white solid. MS (ESI pos. ion) m/z: 414 (MH+). Calc'd exact mass for C24H23N5O2: 413.

Workup

stirringstirred for 72 h at 23° C
customReaction
custompartitioned between 9:1 CHCl3/IPA (25 mL) and 1M NaOH (5 mL)
dry with materialOrganic dried over MgSO4 the
concentrationconcentrated to a solid from toluene under reduced pressure
customSolid triturated with ACN (2 mL)
filtrationcollected by filtration

Sources & evidence

ORD record: ord-76cc3878099049dbb9f925d642d5aed2
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524900B2

Reaction notes

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