Oxalyl chloride → HCID 25255275, compound

HRID 336302Notes

Reaction equation

HRID 336302 reaction equation
C(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][C:15]=1[C:23]([F:26])([F:25])[F:24].[F:27][C:28]1[CH:29]=[CH:30][C:31]([O:38][CH3:39])=[C:32]([C:34](=[N:36]O)[NH2:35])[CH:33]=1.CCN(C(C)C)C(C)C>>[F:27][C:28]1[CH:29]=[CH:30][C:31]([O:38][CH3:39])=[C:32]([C:34]2[N:35]=[C:18]([C:17]3[CH:21]=[CH:22][C:14]([N:9]4[CH2:10][CH2:11][CH2:12][CH2:13][CH:8]4[CH3:7])=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:16]=3)[O:20][N:36]=2)[CH:33]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 594956554-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acidHCID 723368235-fluoro-N'-hydroxy-2-methoxybenzenecarboximidamide

Product 1

HCID 25255275HCID 25255275, compound

Procedure

Oxalyl chloride (106 μL; 1.25 mmol; 3 eq.), Intermediate 24 (120 mg; 0.42 mmol; 1 eq.), Intermediate 23 (77 mg; 0.42 mmol, 1 eq.) and DIEA (216 μL; 1.25 mmol; 3 eq.) were reacted according to general procedure 2. Purification by preparative HPLC (increasing amount of 0.1% TFA in CH3CN, in 0.1% TFA in water) afforded the title compound as a yellow solid.

Workup

  1. customPurification
  2. temperatureby preparative HPLC (increasing amount of 0.1% TFA in CH3CN, in 0.1% TFA in water)

Sources & evidence

ORD record
ord-58c58d54cfcd4da7af7ae88a82b8effe
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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