Novoldiamine → HCID 45377645, compound

HRID 1773002Notes

Reaction equation

HRID 1773002 reaction equation
F[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([OH:18])[CH:10]=[CH:11][C:12]=3[OH:17])[C:7](=[O:19])[C:6]=2[C:5](F)=[C:4]([F:21])[C:3]=1[F:22].[NH2:23][CH:24]([CH2:26][CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH3:25]>C(Cl)Cl>[CH2:30]([N:29]([CH2:32][CH3:33])[CH2:28][CH2:27][CH2:26][CH:24]([NH:23][C:5]1[C:6]2[C:7](=[O:19])[C:8]3[C:13](=[C:12]([OH:17])[CH:11]=[CH:10][C:9]=3[OH:18])[C:14](=[O:16])[C:15]=2[C:2]([NH:23][CH:24]([CH2:26][CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH3:25])=[C:3]([F:22])[C:4]=1[F:21])[CH3:25])[CH3:31]

Participants

4

Reactant 2

HCID 78953NovoldiamineHCID 35272671,2,3,4-Tetrafluoro-5,8-dihydroxyanthraquinone

Product 1

HCID 45377645HCID 45377645, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,2,3,4-tetrafluoro-5,8-dihydroxyanthraquinone (0.47 g, 1.5 mmol) and 2-Amino-5-diethylaminopentane (2.3 mL) in CH2Cl2 (20 mL) was stirred at room temperature for 12 hours. After evaporation of the solvents, the residue was purified by silica gel chromatography using isocratic solvent system of CH2Cl2/MeOH/Et3N (100:10:1) yielding 364 mgs of Dye 2 as dark blue product. Abs (max, PBS pH 7.4)=667 nm; Em=700 nm. The structure of Dye 2 is given below:

Workup

  1. customAfter evaporation of the solvents
  2. customthe residue was purified by silica gel chromatography
  3. customyielding 364 mgs of Dye 2 as dark blue product

Sources & evidence

ORD record
ord-24dbb98a467142b58d79a0016a69e9f5
Source dataset
uspto-grants-2016_02
Patent number
US09250249B2

Reaction notes

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