Hydrochloric Acid → HCID 178465659, compound

HRID 539003Notes

Reaction equation

[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[CH:17][C:18]([C:19]3[CH:28]=[CH:27][C:22]([C:23]([NH:25][NH2:26])=[O:24])=[CH:21][CH:20]=3)=[C:12]2[N:11]=1)([CH3:3])[CH3:2].Cl.[C:30](=[NH:35])(OCC)[CH3:31].C(N(CC)CC)C.Cl>C1COCC1.CN(C=O)C.O>[NH:35]=[C:30]([NH:26][NH:25][C:23](=[O:24])[C:22]1[CH:27]=[CH:28][C:19]([C:18]2[CH:17]=[N:16][N:13]3[CH:14]=[CH:15][C:10]([N:5]4[C@@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:8][O:7][C:6]4=[O:9])=[N:11][C:12]=23)=[CH:20][CH:21]=1)[CH3:31]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of (S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide (Example 9, Step 2; 95 mg, 0.25 mmol) in a mixture of THF (2 mL) and DMF (1 mL) at ambient temperature was added ethyl acetimidate HCl salt (37 mg, 0.30 mmol) and triethylamine (45 μL, 0.32 mmol). The reaction mixture was stirred at 0° C. for 2 hours followed by stirring at ambient temperature for 17 hours. The mixture was poured into water, neutralized with dilute aqueous HCl, extracted with EtOAc, dried over MgSO4, and concentrated to afford 40 mg (38%) of (S)—N′-(1-imino ethyl)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide which was triturated with dichloromethane. LCMS (APCI+) m/z 422.1 [M+H]+.

Workup

stirringby stirring at ambient temperature for 17 hours
extractionextracted with EtOAc
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-8a1ec68d7a404a94879997dad6b10175
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865726B2

Reaction notes

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