Oxalyl chloride → HCID 25256566, compound

HRID 336285Notes

Reaction equation

HRID 336285 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:14]=[C:13]([C:15]([OH:17])=O)[CH:12]=[CH:11][C:10]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24].O[N:26]=[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][CH3:36])[NH2:28].CCN(C(C)C)C(C)C>>[CH3:7][O:8][C:9]1[CH:14]=[C:13]([C:15]2[O:17][N:28]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])[N:26]=2)[CH:12]=[CH:11][C:10]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24]

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 4652214N-Hydroxy-2-methoxy-benzamidineHCID 180010763-Methoxy-4-(2-methylphenyl)benzoic acid

Product 1

HCID 25256566HCID 25256566, compound

Procedure

Oxalyl chloride (126 μL; 1.49 mmol; 3 eq.), Intermediate 27 (120 mg; 0.5 mmol; 1 eq.), Intermediate 1 (82 mg; 0.5 mmol, 1 eq.) and DIEA (256 μL; 1.49 mmol; 3 eq.) were reacted according to general procedure 2. Purification by precipitation from DCM/n-pentane afforded the title compound as a brown solid.

Workup

  1. customPurification
  2. customby precipitation from DCM/n-pentane

Sources & evidence

ORD record
ord-bb8fca81569a4cddb674e06a2f90b445
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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