Fluorescein 5-isothiocyanate → HCID 86691604, compound

HRID 331678Notes

Reaction equation

HRID 331678 reaction equation
C(N(CC)C(C)C)(C)C.[NH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([NH:27][C:28]2[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=2[C:30]([OH:32])=[O:31])=[CH:22][C:21]=1[Cl:37].[CH:38]1[C:43]([N:44]=[C:45]=[S:46])=[CH:42][C:41]2[C:47]([O:49][C:50]3([C:60]4[CH:61]=[CH:62][C:63]([OH:65])=[CH:64][C:59]=4[O:58][C:52]4[CH:53]=[C:54]([OH:57])[CH:55]=[CH:56][C:51]3=4)[C:40]=2[CH:39]=1)=[O:48]>CN(C=O)C>[Cl:37][C:21]1[CH:22]=[C:23]([NH:27][C:28]2[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=2[C:30]([OH:32])=[O:31])[CH:24]=[C:25]([Cl:26])[C:20]=1[O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][NH:10][C:45]([NH:44][C:43]1[CH:42]=[C:41]2[C:40](=[CH:39][CH:38]=1)[C:50]1([C:51]3[CH:56]=[CH:55][C:54]([OH:57])=[CH:53][C:52]=3[O:58][C:59]3[C:60]1=[CH:61][CH:62]=[C:63]([OH:65])[CH:64]=3)[O:49][C:47]2=[O:48])=[S:46]

Participants

5

Reactant 3

HCID 18730Fluorescein 5-isothiocyanateHCID 81531DiisopropylethylamineHCID 67127135HCID 67127135, compound

Product 1

HCID 86691604HCID 86691604, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (10 μL, 0.057 mmol) was added to a solution of the compound 4 (1.9 mg, 0.0035 mmol) and fluorescein isothiocyanate (FITC) (1.2 mg, 0.003 mmol) in DMF (1.0 ml) and the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was subjected to flash column chromatography (silica gel, 1-20% methanol/methylene chloride) to give the desired compound 5 (1.5 mg, 52% yield); 1H NMR (CD3OD, 400 MHz) δ 8.14-8.10 (m, 1H), 7.88 (dd, 1H, J=2.0 Hz, 8.0 Hz), 7.80-7.62 (m, 2H), 7.34-7.30 (m, 1H), 7.24-7.18 (m, 1H), 7.18-7.12 (m, 3H), 6.86-6.78 (m, 1H), 6.72-6.64 (m, 3H), 6.54-6.50 (m, 2H), 4.21-4.04 (m, 4H), 3.92-3.66 (m, 8H); HRMS (ESI+) m/z: calcd for C40H33Cl2N3O10S+H+ 818.1342; found 818.1328 (M+H+).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-817e3c7844134f15953a7a78bf5d7a2a
Source dataset
uspto-grants-2014_11
Patent number
US08877795B2

Reaction notes

Loading…