Phosgene → 1-(cis-2-methyl-cyclohexyl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

HRID 905929노트

반응식

HRID 905929 반응식
[C:1](Cl)(Cl)=[O:2].[CH3:5][Si:6]([CH3:22])([CH3:21])[CH2:7][CH2:8][O:9][CH2:10][N:11]1[C:15]2=[N:16][CH:17]=[C:18]([NH2:20])[N:19]=[C:14]2[CH:13]=[CH:12]1.C(N(C(C)C)CC)(C)C.Cl.[CH3:33][C@H:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]1[NH2:40]>ClCCl>[CH3:33][C@H:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]1[NH:40][C:1]([NH:20][C:18]1[N:19]=[C:14]2[CH:13]=[CH:12][N:11]([CH2:10][O:9][CH2:8][CH2:7][Si:6]([CH3:22])([CH3:21])[CH3:5])[C:15]2=[N:16][CH:17]=1)=[O:2]

참가 물질

6

반응물 4

HCID 6371PhosgeneHCID 81531Diisopropylethylamine2회HCID 127142502-Methylcyclohexylamine hydrochloride, (1R,2S)-HCID 593633695-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine

생성물 1

HCID 673850991-(cis-2-methyl-cyclohexyl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea수율 55%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Phosgene (ca. 20% in toluene, 0.9 mL) was added to a 0° C. solution of 5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine (0.300 g, 1.1 mmol) and diisopropylethylamine (0.6 mL, 3.4 mmol) in 10 mL of dichloromethane. The mixture was stirred for 10 min., then cis-2-methylcyclohexylamine hydrochloride (prepared as in Knupp, G. Chem. Ber. 1984, 117(6), 2076-98, using racemic α-methylbenzylamine) (0.249 g, 1.6 mmol) was added as a solution in 2 mL of dichloromethane with a few added drops of diisopropylethylamine. The mixture was stirred for 40 min., then concentrated to a residue. Column chromatography afforded 0.25 g (55%) of 1-(cis-2-methyl-cyclohexyl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea.

후처리

  1. stirringThe mixture was stirred for 40 min.
  2. concentrationconcentrated to a residue

출처 및 근거

ORD 기록
ord-beded02aa3724a42bad32e2cac7d6755
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012974B2

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