1,1'-Carbonyldiimidazole → HCID 46206100, compound

HRID 2366465Notes

Reaction equation

HRID 2366465 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:6][C:5]=1[F:22])(O)=O.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.Cl.[NH2:37][C:38]1[C:46]([NH2:47])=[CH:45][CH:44]=[CH:43][C:39]=1[C:40]([NH2:42])=[O:41]>N1C=CC=CC=1.CN(C=O)C>[C:40]([C:39]1[C:38]2[N:37]=[C:1]([C:4]3[CH:9]=[CH:8][C:7]([CH:10]4[CH2:14][CH2:13][CH2:12][N:11]4[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:6][C:5]=3[F:22])[NH:47][C:46]=2[CH:45]=[CH:44][CH:43]=1)(=[O:41])[NH2:42]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 534228072,3-Diaminobenzamide dihydrochlorideHCID 69261508HCID 69261508, compound

Product 1

HCID 46206100HCID 46206100, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of EXAMPLE 50D (1.48 g) in pyridine (5 mL) and DMF (5 mL) was added CDI (0.856 g). The solution was stirred at 45° C. for 2 hours, treated with 2,3-diaminobenzamide dihydrochloride (1.08 g), stirred at ambient temperature for 18 hours and concentrated. The concentrate was dissolved in acetic acid (30 mL), and this solution was heated at 80° C. for 3 hours and concentrated. The concentrate was dissolved in ethyl acetate, washed with sodium bicarbonate solution and brine and concentrated. The concentrate was flash chromatographed on silica gel with 0-15% methanol in 2:1 ethyl acetate/hexane.

Workup

  1. stirringstirred at ambient temperature for 18 hours
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in acetic acid (30 mL)
  4. temperaturethis solution was heated at 80° C. for 3 hours
  5. concentrationconcentrated
  6. dissolutionThe concentrate was dissolved in ethyl acetate
  7. washwashed with sodium bicarbonate solution and brine
  8. concentrationconcentrated
  9. customchromatographed on silica gel with 0-15% methanol in 2:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-e92674a8256745a6832b71e8a210bfe7
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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