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

HRID 2215585

반응식

HRID 2215585 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f41ec1298a764116af97233c8cc6fb57
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109219B2

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