Oxalyl chloride → HCID 25255174, compound

HRID 1950869Notes

Reaction equation

HRID 1950869 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][C:34]([F:37])([F:36])[F:35])[NH2:26].CCN(C(C)C)C(C)C>>[CH3:7][C:8]1[CH:9]=[C:10]([C:11]2[O:13][N:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][C:34]([F:35])([F:36])[F:37])[N:24]=2)[CH:14]=[CH:15][C:16]=1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 2794708N'-hydroxy-2-(trifluoromethoxy)benzenecarboximidamideHCID 337808373-Methyl-4-(1-piperidinyl)benzoic acid

Product 1

HCID 25255174HCID 25255174, compound

Procedure

Oxalyl chloride (139 μL; 1.64 mmol; 3 eq.), Intermediate 33 (120 mg; 0.55 mmol; 1 eq.), Intermediate 2 (120 mg; 0.55 mmol, 1 eq.) and DIEA (2834; 1.64 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography (c-hexane/ethyl acetate, 95/5) afforded the title compound as a yellow oil.

Workup

  1. customPurification by column chromatography (c-hexane/ethyl acetate, 95/5)

Sources & evidence

ORD record
ord-3d0ad26076f44d14b302f67fd072b99b
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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