1,1'-Carbonyldiimidazole → HCID 66758835, compound

HRID 564226Notes

Reaction equation

HRID 564226 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17]1[S:21][C:20]([C:22](O)=O)=[CH:19][CH:18]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[Cl-].[Cl-].[NH2:39][C:40]1[C:48]([NH2:49])=[CH:47][CH:46]=[CH:45][C:41]=1[C:42]([NH2:44])=[O:43]>N1C=CC=CC=1.CN(C=O)C>[C:42]([C:41]1[C:40]2[N:39]=[C:22]([C:20]3[S:21][C:17]([CH:12]4[CH2:13][CH2:14][CH2:15][CH2:16][N:11]4[C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:10])=[CH:18][CH:19]=3)[NH:49][C:48]=2[CH:47]=[CH:46][CH:45]=1)(=[O:43])[NH2:44]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 66760304HCID 66760304, compoundHCID 131729295HCID 131729295, compound

Product 1

HCID 66758835HCID 66758835, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of EXAMPLE 28D (0.35 g) in pyridine (10 mL) and DMF (10 mL) was added CDI (0.23 g), and the mixture was heated at 40° C. for 1 hour. 2,3-Diaminobenzamide dichloride (0.22 g) was added, and the mixture stirred at ambient temperature overnight and concentrated. The concentrate was stirred in acetic acid (20 mL) at 80° C. for 4 hours and concentrated. The concentrate was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The extract was washed with water and concentrated, and the concentrate was flash chromatographed on silica gel with 40-80% ethyl acetate in hexane.

Workup

  1. concentrationconcentrated
  2. stirringThe concentrate was stirred in acetic acid (20 mL) at 80° C. for 4 hours
  3. concentrationconcentrated
  4. customThe concentrate was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  5. washThe extract was washed with water
  6. concentrationconcentrated
  7. customchromatographed on silica gel with 40-80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-00436ec2a94c48ecaa896d1670445181
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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