2,4,6-Trimethylbenzoic acid → HCID 24872066, compound

HRID 1424314Notes

Reaction equation

HRID 1424314 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[O:38][C:39](=[O:70])[CH:40]([NH2:69])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([N:48]2[CH2:53][CH2:52][CH:51]([CH2:54][N:55](C(OC(C)(C)C)=O)[C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][N:57]=3)[CH2:50][CH2:49]2)=[CH:44][CH:43]=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[N:57]1[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=1[NH:55][CH2:54][CH:51]1[CH2:52][CH2:53][N:48]([C:45]2[CH:44]=[CH:43][C:42]([CH2:41][CH:40]([NH:69][C:4](=[O:6])[C:3]3[C:7]([CH3:12])=[CH:8][C:9]([CH3:11])=[CH:10][C:2]=3[CH3:1])[C:39]([OH:70])=[O:38])=[CH:47][CH:46]=2)[CH2:49][CH2:50]1

Participants

7

Reactant 4

HCID 101942,4,6-Trimethylbenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57660944HCID 57660944, compound

Product 1

HCID 24872066HCID 24872066, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 202 mg (1.23 mmol) of 2,4,6-trimethylbenzoic acid, 467 mg (1.23 mmol) HATU, 300 mg (0.64 mmol) of (4) and 660 μl (3.85 mmol) DIPEA in 5 ml DMF were stirred at room temperature over night. The reaction mixture was diluted with 100 ml ethyl acetate, washed 3 times with 2 N NaOH/brine (2:1) and once with brine and dried over Na2SO4. The solvent was then removed under reduced pressure.

Workup

  1. washwashed 3 times with 2 N NaOH/brine (2:1)
  2. dry with materialonce with brine and dried over Na2SO4
  3. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-da657c43262647d68a683c04b91c9a9b
Source dataset
uspto-grants-2015_01
Patent number
US08927534B2

Reaction notes

Loading…