Triethylamine → 5-(2-(3-(3-Diethylaminopropyl)ureido)pyridin-4-ylamino)indole-1-carboxylic acid phenylamide

HRID 2215585

Reaction equation

HRID 2215585 reaction equation
[C:1]1([NH:7][C:8]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([NH:19][C:20]4[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[CH:21]=4)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:35](OC1C=CC=CC=1)=[O:36].[CH2:44]([N:46]([CH2:51][CH3:52])[CH2:47][CH2:48][CH2:49][NH2:50])[CH3:45]>O1CCCC1>[C:1]1([NH:7][C:8]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([NH:19][C:20]4[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:35]([NH:50][CH2:49][CH2:48][CH2:47][N:46]([CH2:51][CH3:52])[CH2:44][CH3:45])=[O:36])[CH:21]=4)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 61011N,N-Diethyl-1,3-propanediamineHCID 210548085-(2-Aminopyridin-4-ylamino)indole-1-carboxylic acid phenylamide

Product 1

HCID 210548065-(2-(3-(3-Diethylaminopropyl)ureido)pyridin-4-ylamino)indole-1-carboxylic acid phenylamideYield 3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(2-Aminopyridin-4-ylamino)indole-1-carboxylic acid phenylamide (69 mg, 0.20 mmol, Production example 201-3) was dissolved in tetrahydrofuran (14 ml); triethylamine (0.055 ml, 0.40 mmol) was added thereto; and phenyl chloroformate (0.038 ml, 0.30 mmol) was added while stirring and cooled by ice. A portion of 7.0 ml of this reaction mixture was transferred to another vessel; and the remaining portion of the reaction mixture was concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (1.0 ml); the similar reaction to Example 201 was performed using N,N-diethyl-1,3-diaminopropane (0.047 ml, 0.30 mmol); the crude product obtained was purified by a TLC plate (Fuji Silysia NH, developing solvent:ethyl acetate/ethanol=10/1); and the obtained crystals were suspended in ethyl acetate, filtered off, and dried to yield the title compound (3 mg, 0.006 mmol) as colorless crystals.

Workup

  1. temperaturecooled by ice
  2. concentrationand the remaining portion of the reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in N,N-dimethylformamide (1.0 ml)
  4. customthe similar reaction to Example 201
  5. customthe crude product obtained
  6. customwas purified by a TLC plate (Fuji Silysia NH, developing solvent:ethyl acetate/ethanol=10/1)
  7. filtrationfiltered off
  8. customdried

Sources & evidence

ORD record
ord-f41ec1298a764116af97233c8cc6fb57
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Linked notes

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