Oxalyl chloride → HCID 25255381, compound

HRID 336312Notes

Reaction equation

HRID 336312 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[C:17]1[C:18]([CH3:23])=[N:19][CH:20]=[CH:21][CH:22]=1)[C:11]([OH:13])=O.[F:24][C:25]1[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([C:31](=[N:33]O)[NH2:32])[CH:30]=1.CCN(C(C)C)C(C)C>>[F:24][C:25]1[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([C:31]2[N:32]=[C:11]([C:10]3[CH:14]=[CH:15][C:16]([C:17]4[C:18]([CH3:23])=[N:19][CH:20]=[CH:21][CH:22]=4)=[C:8]([CH3:7])[CH:9]=3)[O:13][N:33]=2)[CH:30]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 59606547HCID 59606547, compoundHCID 723368235-fluoro-N'-hydroxy-2-methoxybenzenecarboximidamide

Product 1

HCID 25255381HCID 25255381, compound

Procedure

Oxalyl chloride (84 mg; 0.66 mmol; 3 eq.), Intermediate 37 (50 mg; 0.22 mmol; 1 eq.), Intermediate 23 (41 mg; 0.22 mmol, 1 eq.) and DIEA (85 mg; 0.66 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography c-hexane/ethyl acetate, 90/10 then 85/15) afforded the title compound as a white solid.

Workup

  1. customPurification by column chromatography c-hexane/ethyl acetate, 90/10

Sources & evidence

ORD record
ord-55b00f1f64b048539737db872c6c0d3c
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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