Oxalyl chloride → HCID 25255279, compound

HRID 1950878Notes

Reaction equation

HRID 1950878 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.O[N:24]=[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34])[NH2:26].CCN(C(C)C)C(C)C>>[CH3:34][O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:25]1[N:24]=[C:11]([C:10]2[CH:14]=[CH:15][C:16]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[C:8]([CH3:7])[CH:9]=2)[O:13][N:26]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 4652214N-Hydroxy-2-methoxy-benzamidineHCID 337808373-Methyl-4-(1-piperidinyl)benzoic acid

Product 1

HCID 25255279HCID 25255279, compound

Procedure

Oxalyl chloride (139 μL; 1.64 mmol; 3 eq.), Intermediate 33 (120 mg; 0.55 mmol; 1 eq.), Intermediate 1 (91 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 an orange 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-c5a824cbf86e451ab67739e61112cc59
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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