1,1'-Carbonyldiimidazole → HCID 25000363, compound

HRID 1360322Notes

Reaction equation

HRID 1360322 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)[CH2:4]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:30][C:31]1[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[C:32]=1[C:33](O)=[O:34]>C(#N)C.O.CN(C=O)C>[CH3:17][N:2]([CH3:1])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([C:10]3[O:12][C:33](=[O:34])[C:32]4[C:36]([CH3:40])=[CH:37][CH:38]=[CH:39][C:31]=4[N:30]=3)=[CH:13][CH:14]=[CH:15][N:16]=2)[CH2:4]1

Participants

7

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1512106-Methylanthranilic acidHCID 59755964HCID 59755964, compound

Product 1

HCID 25000363HCID 25000363, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A solution of compound C (133 mg, 0.56 mmol) and CDI (91 mg, 0.56 mmol) in anhydrous acetonitrile (1.0 mL) was stirred for 1 hour at ambient temperature. 2-Amino-6-methyl-benzoic acid (41 mg, 0.27 mmol) was added, and the mixture was stirred at 60° C. overnight. The reaction solution was diluted with water (2 mL) and DMF (2 mL), filtered, then purified by C18 reverse phase chromatography to afford compound 46 as an off-white powder (11 mg, 35% yield). 1H-NMR δ (CDCl3): 8.32 (dd, 1H, J=4.8 Hz, J=2.0 Hz), 8.09 (dd, 1H, J=8.0 Hz, J=1.6 Hz), 7.68 (t, 1H, J=15.6 Hz, J=0.8 Hz), 7.52 (t, 1H, J=4.0 Hz, J=7.6 Hz), 7.33 (d, 1H, J=7.2 Hz), 6.82 (dd, 1H, J=8 Hz, J=4.8 Hz), 3.95 (br s, 1H), 3.81 (br s, 1H), 3.57-3.64 (m, 2H), 3.48-3.53 (m, 2H), 2.83 (s, 3H), 2.64 (br s, 6H), 2.30 (br s, 1H). ESMS: 351.1 [M+H]+.

Workup

  1. filtrationfiltered
  2. custompurified by C18 reverse phase chromatography

Sources & evidence

ORD record
ord-a120717ba3444a0eb250b10070bc681e
Source dataset
uspto-grants-2011_02
Patent number
US07879846B2

Reaction notes

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