N,N-Dimethylethylenediamine → HCID 16124789, compound

HRID 1945413Notes

Reaction equation

HRID 1945413 reaction equation
[C:1]12([C:11]3[CH:31]=[CH:30][C:14]([O:15][CH2:16][C:17]([NH:19][C:20]4[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=4[OH:29])[C:23](O)=[O:24])=[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.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH3:65][N:66]([CH3:70])[CH2:67][CH2:68][NH2:69].CCN(C(C)C)C(C)C>CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C.CO>[C:1]12([C:11]3[CH:31]=[CH:30][C:14]([O:15][CH2:16][C:17]([NH:19][C:20]4[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=4[OH:29])[C:23]([NH:69][CH2:68][CH2:67][N:66]([CH3:70])[CH3:65])=[O:24])=[O:18])=[CH:13][CH:12]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

7

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 161247274-Hydroxy-3-[[2-(4-tricyclo[3.3.1.13,7]dec-1-ylphenoxy)acetyl]amino]benzoic acid

Product 1

HCID 16124789HCID 16124789, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 70262,4,6-Tris((dimethylamino)methyl)phenolSolvent

Procedure

3-[2-(4-adamantan-1-yl-phenoxy)acetylamino]-4-hydroxy-benzoic acid (60.1 mg, 0.14 mmol) and PyBOP (148.3 mg, 0.29 mmol) in DMF 3.0 ml was added N,N-dimethylethylenediamine (25.1 mg, 0.29 mmol, 0.03 ml) and DIPEA (0.05 ml, 0.29 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(CH2C2:MeOH=7:1) to give 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-N-(2-dimethylamino-ethyl)-4-hydroxy-benzamide as a yellow solid (20.2 mg, 28.7% 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(CH2C2

Sources & evidence

ORD record
ord-29193dc3123a4d239a174754082007f7
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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