Sodium hydride → HCID 86620089, compound

HRID 1788334Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([C:25]4[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=4)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.[F:32][C:33]([F:44])([F:43])[CH2:34][O:35]S(C(F)(F)F)(=O)=O.[H-].[Na+]>CN(C=O)C>[F:32][C:33]([F:44])([F:43])[C:34]([OH:31])=[O:35].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([C:25]4[CH:26]=[CH:27][C:28]([O:31][CH2:34][C:33]([F:44])([F:43])[F:32])=[CH:29][CH:30]=4)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Into a 25 mL glass pressure tube fitted with Teflon screw cap and magnetic bar is placed 4-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-yl]phenol (Example 7 before reverse phase HPLC purification); 0.100 g, 0.25 mmol), DMF (2 mL), trifluoro-methanesulfonic acid 2,2,2-trifluoroethyl ester (0.064 g 0.275 mmol), and 60% NaH (11 mg, 0.275 mmol). The cap is positioned, and mixture heated in oil bath at 70° C. for 16 h. The reaction is quenched with 15 mL water, giving 67 mg of precipitate as the title compound as a free base. The purified product, 36.4 mg (24%), is obtained by freeze drying appropriate fractions (based on MS analysis) from reverse phase HPLC using Waters Symmetry C18 column with a gradient of 10 to 70% B in A, where A is water containing 0.1% TFA and B is CH3CN containing 0.1% TFA.

Workup

customcap
custommagnetic bar is placed
customThe reaction is quenched with 15 mL water

Sources & evidence

ORD record: ord-9c29f6f8319341f29ceb15208efbf7dd
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511065B2

Reaction notes

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