Oxalyl chloride → HCID 59606536, compound

HRID 336279Notes

Reaction equation

HRID 336279 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][C:16]=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]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:23][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:17][C:16]=1[CH3:24]

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 4652214N-Hydroxy-2-methoxy-benzamidineHCID 219477594-(2-Methoxyphenyl)-3-methylbenzoic acid

Product 1

HCID 59606536HCID 59606536, compound

Procedure

Oxalyl chloride (126 μL; 1.5 mmol; 3 eq.), Intermediate 26 (120 mg; 0.5 mmol; 1 eq.), Intermediate 1 (82 mg; 0.5 mmol, 1 eq.) and DIEA (256 μL; 1.5 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography c-hexane/ethyl acetate, 90/10) followed by precipitation from n-pentane afforded the title compound as a white solid.

Workup

  1. customPurification by column chromatography c-hexane/ethyl acetate, 90/10)
  2. customfollowed by precipitation from n-pentane

Sources & evidence

ORD record
ord-9654d971965141559f56fbbe1f352e58
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

Loading…