Isopropyl isocyanate → N-{2-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-N'-(1-methylethyl)urea

HRID 9437

반응식

HRID 9437 반응식
[NH2:1][CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][C:12]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)=[CH:11][C:10]=3[N:9]=[C:8]([NH2:23])[C:7]=2[N:6]=[C:5]1[CH2:24][O:25][CH2:26][CH3:27].[CH:28]([N:31]=[C:32]=[O:33])([CH3:30])[CH3:29]>C(Cl)(Cl)Cl>[NH2:23][C:8]1[C:7]2[N:6]=[C:5]([CH2:24][O:25][CH2:26][CH3:27])[N:4]([CH2:3][CH2:2][NH:1][C:32]([NH:31][CH:28]([CH3:30])[CH3:29])=[O:33])[C:16]=2[C:15]2[CH:14]=[CH:13][C:12]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:11][C:10]=2[N:9]=1

참가 물질

4

반응물 2

HCID 61277Isopropyl isocyanateHCID 219841051-(2-Aminoethyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 21984297N-{2-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-N'-(1-methylethyl)urea수율 28.5%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of 1-(2-aminoethyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (2.50 g, 6.90 mmol) in chloroform (50 mL) was treated with isopropyl isocyanate (0.65 mL, 6.9 mmol) according to the method described in Examples 377–379. The crude product was purified by column chromatography on silica gel (eluting with 94:6 chloroform:methanol) followed by trituration with acetonitrile (15 mL/g) at 95° C. The mixture was cooled in an ice bath, isolated by filtration, and dried for one hour in a vacuum oven at 100° C. to provide 0.88 g of N-{2-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-N′-(1-methylethyl)urea as a white solid, mp 194–196° C.

후처리

  1. customThe crude product was purified by column chromatography on silica gel (eluting with 94:6 chloroform:methanol)
  2. customfollowed by trituration with acetonitrile (15 mL/g) at 95° C
  3. temperatureThe mixture was cooled in an ice bath
  4. customisolated by filtration
  5. customdried for one hour in a vacuum oven at 100° C.

출처 및 근거

ORD 기록
ord-d16d8d902d0c45cfb7ea9fa85a26dbda
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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