1,1'-Carbonyldiimidazole → HCID 25028713, compound

HRID 1436462Notes

Reaction equation

HRID 1436462 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]([NH:25][CH2:26][CH2:27][OH:28])[S:23][CH:24]=2)=[CH:16][CH:15]=1>O1CCCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:21]=[C:22]([N:25]3[CH2:26][CH2:27][O:28][C:1]3=[O:2])[S:23][CH:24]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86618621HCID 86618621, compound

Product 1

HCID 25028713HCID 25028713, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Carbonyldiimidazole (0.16 g, 1 mmol) was added to a solution of 2-{[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino}ethanol (0.15 g, 0.58 mmol), prepared in the previous step, in dry tetrahydrofuran (5 mL) at room temperature under nitrogen. After 72 h, the mixture was evaporated and the residue purified by silica gel column chromatography (ethyl acetate:hexanes, 1:3 as eluant) to afford the title compound (9.8 mg, 5%) as a white solid, MS (ES) m/z 281 [M+H]+. ANLC 96.4%@210 nm, 96.2%@230 nm; RT=8.0 min, the Xterra® MS C18m instrument, 3.5μ, 4.6×50 mm column, 0.8 mL/min, Grad: 5/95-95/5 (A) the PIC™ B6 reagent (5 mM Hex. Sulfonic Acid); (B) AcCN.

Workup

  1. customthe mixture was evaporated
  2. customthe residue purified by silica gel column chromatography (ethyl acetate:hexanes, 1:3 as eluant)

Sources & evidence

ORD record
ord-2e2ab1aa9a6e44888871eae7835ad524
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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