Methanol → HCID 178513229, compound

HRID 77356Notes

Reaction equation

HRID 77356 reaction equation
O=C1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:5][N:4]2[C:18]([C:21]#[N:22])=[CH:19][CH:20]=[C:3]12.Cl.[NH2:24][OH:25].C(N(CC)C(C)C)(C)C.[CH3:35][OH:36]>C(Cl)Cl.CN(C)C=O>[OH:25][NH:24][C:21]([C:18]1[N:4]2[CH:5]=[C:6]([C:8]3[CH:9]=[CH:10][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=3)[NH:7][C:35](=[O:36])[C:3]2=[CH:20][CH:19]=1)=[NH:22]

Participants

7

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 727149431-Oxo-3-(4-trifluoromethyl-phenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carbonitrile

Product 1

HCID 178513229HCID 178513229, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-oxo-3-(4-trifluoromethyl-phenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carbonitrile (Example 2), (0.05 g, 0.16 mmol), hydroxylamine hydrochloride (15 mg, 0.22 mmol) and N,N-diisopropylethylamine (86.4 μL, 0.49 mmol,) was stirred in methylene chloride (0.5 mL), methanol (0.5 mL) and N,N-dimethylformamide (0.2 mL) at 45° C. for 2 d. At this time, the resulting solids were collected by filtration to afford N-hydroxy-1-oxo-3-(4-trifluoromethyl-phenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carboxamidine (40 mg, 70%) as an off-white solid. 1H NMR (methanol-d4) δ ppm 7.83 (q, J=8.4 Hz, 4H), 7.73 (s, 2H), 7.37 (s, 1H). LC-MS calcd. for C15H12F3N4O2 [(M+H)+] 337, obsd. 337.0.

Workup

  1. filtrationAt this time, the resulting solids were collected by filtration

Sources & evidence

ORD record
ord-498ad876749b4faf813b54f96f693472
Source dataset
uspto-grants-2014_09
Patent number
US08841299B2

Reaction notes

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