Water → HCID 13800119, compound

HRID 2166369Notes

Reaction equation

HRID 2166369 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:8]=2[C:9]2[C:10]([CH2:23][O:24][CH3:25])=[C:11]([C:20](O)=[O:21])[N:12]=[CH:13][C:14]=2[NH:15]3)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:40]([NH2:43])([CH3:42])[CH3:41].O>CN(C)C=O>[CH:40]([NH:43][C:20]([C:11]1[N:12]=[CH:13][C:14]2[NH:15][C:16]3[C:8]([C:9]=2[C:10]=1[CH2:23][O:24][CH3:25])=[C:7]([O:6][C:5]1[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH:19]=[CH:18][CH:17]=3)=[O:21])([CH3:42])[CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 13800024HCID 13800024, compound

Product 1

HCID 13800119HCID 13800119, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

382 mg of 5-(4-chlorophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid in 10 ml of dimethylformamide is mixed with 380 mg of carbonyldiimidazole. After 2 hours stirring at room temperature, 1 ml of isopropylamine is added and stirred overnight. After mixing with water, it is extracted with ethyl acetate. The ethyl acetate phase is dried, filtered and concentrated. The residue is chromatographed over silica gel with methylene chloride: acetone=1:1 as eluant. 90 mg of 5-(4-chlorophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropylamide with a melting point of 255° C. is obtained.

Workup

  1. stirringstirred overnight
  2. extractionis extracted with ethyl acetate
  3. dry with materialThe ethyl acetate phase is dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed over silica gel with methylene chloride

Sources & evidence

ORD record
ord-3f5a875590294f54a6fcaf74715ce6df
Source dataset
uspto-grants-1990_07
Patent number
US04945090

Reaction notes

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