Oxalyl chloride → HCID 25255382, compound

HRID 336313Notes

Reaction equation

[C:1](Cl)(=O)C(Cl)=O.[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][N:15]=1.[F:23][C:24]1[CH:25]=[CH:26][C:27]([O:34][CH3:35])=[C:28]([C:30](=[N:32]O)[NH2:31])[CH:29]=1.CCN(C(C)C)C(C)C>>[F:23][C:24]1[CH:25]=[CH:26][C:27]([O:34][CH3:35])=[C:28]([C:30]2[N:32]=[C:18]([C:17]3[CH:21]=[C:22]([CH3:1])[C:14]([N:9]4[CH2:10][CH2:11][CH2:12][CH2:13][CH:8]4[CH3:7])=[N:15][CH:16]=3)[O:20][N:31]=2)[CH:29]=1

Participants

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 16771415HCID 16771415, compound

HCID 723368235-fluoro-N'-hydroxy-2-methoxybenzenecarboximidamide

Product 1

HCID 25255382HCID 25255382, compound

Procedure

Oxalyl chloride (130 μL; 1.54 mmol; 3 eq.), Intermediate 38 (120 mg; 0.51 mmol; 1 eq.), Intermediate 23 (94 mg; 0.51 mmol, 1 eq.) and DIEA (260 μL; 1.54 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography c-hexane/ethyl acetate, 50/50) afforded the title compound as a white solid.

Workup

customPurification by column chromatography c-hexane/ethyl acetate, 50/50)

Sources & evidence

ORD record: ord-2161fb59dd694f13a87ce5903ebac7c3
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889668B2

Reaction notes

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