2,4,6-Tris((dimethylamino)methyl)phenol → HCID 16124789, compound

HRID 1945414Notes

Reaction equation

HRID 1945414 reaction equation
[C:1]12([C:11]3[CH:31]=[CH:30][C:14]([O:15][CH2:16][C:17]([NH:19]C4C=C(C=CC=4O)C(O)=O)=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:32][N:33]([C:35](ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:34].F[P-](F)(F)(F)(F)F.NCCCN1CC[O:63]CC1.CCN(C(C)C)C(C)C.C[N:76]([CH2:78][C:79]1[CH:84]=[C:83](CN(C)C)[C:82]([OH:89])=[C:81](CN(C)C)[CH:80]=1)[CH3:77]>>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([O:15][CH2:16][C:17]([NH:19][C:83]4[CH:84]=[C:79]([CH:80]=[CH:81][C:82]=4[OH:89])[C:78]([NH:76][CH2:77][CH2:32][N:33]([CH3:35])[CH3:34])=[O:63])=[O:18])=[CH:30][CH:31]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 5

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolHCID 61055N-(3-Aminopropyl)morpholineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 161247274-Hydroxy-3-[[2-(4-tricyclo[3.3.1.13,7]dec-1-ylphenoxy)acetyl]amino]benzoic acid

Product 1

HCID 16124789HCID 16124789, compoundYield 14.5%

Procedure

3-[2-(4-adamantan-1-yl-phenoxy)acetylamino]-4-hydroxy-benzoic acid (50.1 mg, 0.12 mmol), HATU (68.5 mg, 0.18 mmol) in DMF 3.0 ml was added N-(aminopropyl)morpholine (0.18 mmol, 0.03 ml) and DIPEA (0.03 ml, 0.18 mmol) at room temperature. The reaction mixture was separated with ethyl acetate and sodium bicarbonate. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by preparative TLC(CH2Cl2:MeOH=15:1) to give 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-N-(2-dimethylamino-ethyl)-4-hydroxy-benzamide as a yellow solid (9.5 mg, 14.5% yield).

Workup

  1. customThe reaction mixture was separated with ethyl acetate and sodium bicarbonate
  2. dry with materialThe organic phase was dried (MgSO4 anh)
  3. concentrationconcentrated
  4. customThe residue was purified by preparative TLC(CH2Cl2:MeOH=15:1)

Sources & evidence

ORD record
ord-523c127196f945639781dafce51cd47d
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

Loading…