Ethyl difluoroacetate → HCID 178452595, compound

HRID 1509242Notes

Reaction equation

[F:1][CH:2]([F:8])[C:3](OCC)=[O:4].O.[NH2:10][NH2:11].[C:12]1([C:18]2[C:28]([C:29]3[CH:34]=[CH:33][C:32]([C:35]4([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:38][CH2:37][CH2:36]4)=[CH:31][CH:30]=3)=[N:27][C:21]3[O:22][CH2:23][C:24](=S)[NH:25][C:20]=3[CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O>[F:1][CH:2]([F:8])[C:3]([NH:10]/[N:11]=[C:24]1/[NH:25][C:20]2[CH:19]=[C:18]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:28]([C:29]3[CH:30]=[CH:31][C:32]([C:35]4([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:43])[CH3:44])[CH2:36][CH2:37][CH2:38]4)=[CH:33][CH:34]=3)=[N:27][C:21]=2[O:22][CH2:23]/1)=[O:4]

Participants

Conditions

Temperature: 70 °C

Procedure

Ethyl 2,2-difluoroacetate (0.43 ml, 4.10 mmol) and hydrazine monohydrate were heated to 60° C. in N,N-dimethylformamide (1 ml) for 30 minutes to give a colourless solution. Tert-butyl (1-(4-(7-phenyl-2-thioxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (100 mg, 0.205 mmol) was added to the previous solution at room temperature. The resulting mixture was heated to 70° C. for 20 hours. The reaction mixture was concentrated under reduced pressure and the crude material (100 mg, quantitative yield) was used for the next step without further purification. LCMS (Method D): RT=1.37 min, M+1=564.

Workup

customto give a colourless solution
concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-839d9fed66214882a34d64879d27ede4
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

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