Oxalyl chloride → HCID 25255280, compound

HRID 336307Notes

Reaction equation

HRID 336307 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:11]([OH:13])=O.[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:31]=[C:11]([C:10]3[CH:14]=[CH:15][C:16]([N:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[C:8]([CH3:7])[CH:9]=3)[O:13][N:32]=2)[CH:29]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 337808373-Methyl-4-(1-piperidinyl)benzoic acidHCID 723368235-fluoro-N'-hydroxy-2-methoxybenzenecarboximidamide

Product 1

HCID 25255280HCID 25255280, compound

Procedure

Oxalyl chloride (139 μL; 1.64 mmol; 3 eq.), Intermediate 33 (120 mg; 0.55 mmol; 1 eq.), Intermediate 23 (101 mg; 0.55 mmol, 1 eq.) and DIEA (283 μL; 1.64 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 white 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-48faa27ef3d74b59b78c68c6fbd2bd13
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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