Sodium Bicarbonate → HCID 56645935, compound

HRID 510023Notes

Reaction equation

[NH2:1][C:2]1[C:7]([NH:8][C:9](=[O:16])[O:10][C:11]([CH3:15])([CH3:14])[CH2:12]Cl)=[C:6]([NH2:17])[N:5]=[C:4]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[N:19]=2)[N:3]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[NH2:1][C:2]1[C:7]([N:8]2[CH2:12][C:11]([CH3:15])([CH3:14])[O:10][C:9]2=[O:16])=[C:6]([NH2:17])[N:5]=[C:4]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[N:19]=2)[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

500 mg (1.033 mmol) of the compound prepared in example 7A were dissolved in tetrahydrofuran (10 ml), and 1.033 ml of a 1M solution of bis(trimethylsilyl)sodium amide solution in tetrahydrofuran were added at 0° C. After stirring at 0° C. for 5 min, the reaction was stopped by addition of saturated aqueous sodium hydrogencarbonate solution and extracted twice with ethyl acetate. The combined organic phases were dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). 329 mg of the title compound were obtained (71% of theory).

Workup

extractionextracted twice with ethyl acetate
dry with materialThe combined organic phases were dried with sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record: ord-363becb410b34fd692f73a9c9dac69f1
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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