Diethylamine → HCID 21054824, compound

HRID 2376906Notes

Reaction equation

HRID 2376906 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.[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30]C)[CH3:28].ClC(OC1C=CC=CC=1)=[O:36].C(NCC)C>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:30]([N:29]([CH2:32][CH3:33])[CH2:27][CH3:28])=[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 8021DiethylamineHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 210548085-(2-Aminopyridin-4-ylamino)indole-1-carboxylic acid phenylamide

Product 1

HCID 21054824HCID 21054824, compoundYield 2.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(2-Aminopyridin-4-ylamino)indole-1-carboxylic acid phenylamide (69 mg, 0.20 mmol) 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 thereto while cooling with ice and stirring. A portion of 7.0 ml of the reaction mixture was transferred to another vessel and concentrated under reduced pressure. After the residue was dissolved in N,N-dimethylformamide (1.0 ml), the similar reaction to Example 27 was performed by use of diethylamine (0.031 ml, 0.30 mmol). The obtained crude product was purified by TLC plate (Fuji Silysia NH, developing solvent: ethyl acetate) to yield the title compound (2.0 mg, 0.005 mmol) as pale yellow crystals.

Workup

  1. temperaturewhile cooling with ice
  2. concentrationconcentrated under reduced pressure
  3. dissolutionAfter the residue was dissolved in N,N-dimethylformamide (1.0 ml)
  4. customthe similar reaction to Example 27
  5. customThe obtained crude product
  6. customwas purified by TLC plate (Fuji Silysia NH, developing solvent: ethyl acetate)

Sources & evidence

ORD record
ord-490c5dd50a4a492fa00688dc098473d1
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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