Dimethylformamide → HCID 88038425, compound

HRID 1835611Notes

Reaction equation

HRID 1835611 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([CH3:28])([CH3:27])[CH2:25][NH2:26])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)[CH:31]=[O:32].C(N(CC)CC)C.C(ON1C(=O)CCC1=O)(=O)[C:42]1[CH:47]=[CH:46][CH:45]=[N:44][CH:43]=1>C(#N)C.O>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:10]=[C:9]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([CH3:28])([CH3:27])[CH2:25][N:26]([C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)[CH:31]=[O:32])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 870586Succinimidyl NicotinateHCID 23501676HCID 23501676, compound

Product 1

HCID 88038425HCID 88038425, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of 6-(4,6-diphenyl(2-pyridyloxy))-2,2-dimethylhexylamine (0.14 g, 0.373 mmol), N,N-dimethylformamide (4 mL), and triethylamine (0.3 mL) was stirred at room temperature for 10 min. Succinimidyl nicotinate (0.1 g, 0.447 mmol) was added, and the mixture was stirred for 18 h. The mixture was concentrated under high vacuum, and the residue was purified using reverse-phase HPLC (water-acetonitrile containing 0.1 TFA) to afford 0.114 mg (64%) of a white powdered solid. 1H NMR (CDCl3): 8.12-6.80 (m, 16H), 4.54 (t, 2H), 3.43 (t, 2H), 1.90 (m, 6H), 1.05 (s, 6H); ESMS: Calculated for C31H33N3O2, 479.2573 Found 480.2 [M+H]+1; Rt=17.096 min (100% pure, Vydac C18 column; gradient 20 to 100% acetonitrile/water+0.1% TFA over 30 min).

Workup

  1. stirringthe mixture was stirred for 18 h
  2. concentrationThe mixture was concentrated under high vacuum
  3. customthe residue was purified
  4. customto afford 0.114 mg (64%) of

Sources & evidence

ORD record
ord-e310dc8a27f7437cb47f541eb6e56f84
Source dataset
uspto-grants-2004_08
Patent number
US06770259B2

Reaction notes

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