HCID 86614816, compound → HCID 86614823, compound

HRID 1686160Notes

Reaction equation

HRID 1686160 reaction equation
[CH2:1]([N+:8]1[C:16]2[C:11](=[CH:12][C:13]([S:17]([O-:20])(=[O:19])=[O:18])=[CH:14][CH:15]=2)[C:10]([CH3:29])([CH2:21][CH2:22][CH2:23][CH2:24][S:25]([OH:28])(=[O:27])=[O:26])[C:9]=1[CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][N+:39]1[C:47]2[C:42](=[CH:43][C:44]([S:48]([O-:51])(=[O:50])=[O:49])=[CH:45][CH:46]=2)[C:41]([CH3:60])([CH2:52][CH2:53][CH2:54][CH2:55][S:56]([OH:59])(=[O:58])=[O:57])[C:40]=1[CH3:61])([OH:33])=[O:32].C(O)(=O)C.N1C=C[CH:69]=[CH:68][CH:67]=1.C(OC(=O)C)(=O)C>O>[CH2:1]([N+:8]1[C:16]2[C:11](=[CH:12][C:13]([S:17]([O-:20])(=[O:18])=[O:19])=[CH:14][CH:15]=2)[C:10]([CH3:29])([CH2:21][CH2:22][CH2:23][CH2:24][S:25]([OH:28])(=[O:27])=[O:26])[C:9]=1/[CH:30]=[CH:69]/[CH:68]=[CH:67]/[CH:61]=[C:40]1/[N:39]([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][C:31]([OH:33])=[O:32])[C:47]2[C:42]([C:41]/1([CH3:60])[CH2:52][CH2:53][CH2:54][CH2:55][S:56]([OH:59])(=[O:57])=[O:58])=[CH:43][C:44]([S:48]([OH:51])(=[O:50])=[O:49])=[CH:45][CH:46]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 86614816HCID 86614816, compoundHCID 86614821HCID 86614821, compoundHCID 86614824HCID 86614824, compound

Product 1

HCID 86614823HCID 86614823, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

1-Benzyl-2,3-dimethyl-3-(4-sulphobutyl)-3H-indolium-5-sulphonate salt (2 g), 1-(5-carboxypentyl)-2,3-dimethyl-3-(4-sulphobutyl)-3H-indolium-5-sulphonate (2 g) and malonaldehyde bis-phenylimine (2 g) were dissolved in acetic acid: pyridine: acetic anhydride (4.5:4.5:1) (100 ml). The mixture was heated at 90° C. for 2 hours. The mixture went blue/green immediately. A small sample was diluted in water for UV measurement. UV/Vis absorption spectroscopy observed a peak at 650 nm showing formation of Cy5. The reaction mixture was stored overnight at +2° C. The mixture was rotary evaporated to yield an oil. This was pumped under vacuum for several hours to ensure dryness. The sticky solid was washed with acetonitrile (4×500 ml) to yield a dry powder that was filtered and washed with more acetonitrile. The solid was dried under vacuum. Yield: 3.05 g.

Workup

  1. customUV/Vis absorption spectroscopy
  2. customThe mixture was rotary evaporated
  3. customto yield an oil
  4. waitThis was pumped under vacuum for several hours
  5. washThe sticky solid was washed with acetonitrile (4×500 ml)
  6. customto yield a dry powder that
  7. filtrationwas filtered
  8. washwashed with more acetonitrile
  9. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-ad2c1abdf5c24c298728ba36e6ec3b14
Source dataset
uspto-grants-2012_04
Patent number
US08148539B2

Reaction notes

Loading…