1,1'-Carbonyldiimidazole → HCID 86583671, compound

HRID 1884760Notes

Reaction equation

HRID 1884760 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[CH:6][C:5]([C:18](O)=[O:19])=[CH:4][C:3]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1.C([N:38]1[CH:42]=[CH:41]N=C1)(N1C=CN=C1)=O.[C:43]1(NCCCCCCCC)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C>[C:43]1([CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH2:5][CH2:41][CH2:42][NH:38][C:18]([C:5]2[CH:4]=[C:3]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=3)[C:2]([NH2:1])=[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=3)[CH:6]=2)=[O:19])[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

5

Reactant 3

HCID 682631,1'-Carbonyldiimidazole2×HCID 137788N-Octylaniline2×HCID 22237384HCID 22237384, compound

Product 1

HCID 86583671HCID 86583671, compoundYield 181.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2′-amino-3,3″-bis-trifluoromethyl-[1,1′:3′1″]terphenyl-5′-carboxylic acid (0.113 g, 0.27 mmol 1 eq) in DMF (2.7 mL) was added 1,1′-carbonyldiimidazole (0.120 g, 0.74 mmol 2.7 eq) and phenyl octylamine (0.070 mL, 0.35 mmol, 1.3 eq) and the reaction was stirred overnight at rt. Additional 1,1′-carbonyldimidazole (0.124 g, 0.76 mmol 2.8 eq) and phenyl octylamine (0.070 mL, 0.35 mmol, 1.3 eq) was added and stirring was continued overnight. The solids were then filtered off and washed with EtOAc. The filtrate was washed with saturated NaHCO3 solution, 0.1 N HCl and brine. It was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (20% EtOAc:Hexane +1% Formic acid) to afford the title compound (0.150 g, 37%) as a light yellow oil. 1H NMR (DMSO-d6 5 8.20 (t, 1H); 7.81-7.70 (m, 8H); 7.61 (s, 2H); 7.25-7.12 (m, 5H); 4.87 (s, 2H); 3.19 (dd, 2H); 2.52 (t, 2H); 1.50 (m, 4H); 1.28 (m, 8H); IR (KBr) 3540, 3350, 2950, 2850, 1620, 1545, 1480, 1420, 1325, 1180, 1120, 1110, 1080 cm−1; mass spectrum [(+)APCI], m/z 613 (M+H)+; Anal. Calcd. for C35H34F6N2O: C, 68.62; H, 5.59; N, 4.57, Found: C, 67.66; H, 5.96; N, 4.33.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. filtrationThe solids were then filtered off
  4. washwashed with EtOAc
  5. washThe filtrate was washed with saturated NaHCO3 solution, 0.1 N HCl and brine
  6. dry with materialIt was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (20% EtOAc:Hexane +1% Formic acid)

Sources & evidence

ORD record
ord-7633d4a7d2514454b4eca7bb1315c787
Source dataset
uspto-grants-2004_07
Patent number
US06765021B2

Reaction notes

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