Diisopropylethylamine → (R)-tert-butyl 2-(N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxamido)ethylcarbamate

HRID 80993

반응식

HRID 80993 반응식
Cl[C:2]1[C:3]2[C@H:10]([CH3:11])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:12][C:13]1[CH:38]=[CH:37][C:16]([CH2:17][N:18]([CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:19]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:20])=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>C(#N)C.O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]([CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[C:19]([N:21]2[CH2:22][CH2:23][N:24]([C:2]3[C:3]4[C@H:10]([CH3:11])[CH2:9][CH2:8][C:4]=4[N:5]=[CH:6][N:7]=3)[CH2:25][CH2:26]2)=[O:20])=[CH:37][CH:38]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 59670769(R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidineHCID 67135341tert-butyl 2-(N-(4-chlorobenzyl)piperazine-1-carboxamido)ethylcarbamate

생성물 1

HCID 67134584(R)-tert-butyl 2-(N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxamido)ethylcarbamate수율 30.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

(R)-4-Chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (46 mg, 0.27 mmol, 1.1 eq.) was added to a solution of the tert-butyl 2-(N-(4-chlorobenzyl)piperazine-1-carboxamido)ethylcarbamate (100 mg, 0.25 mmol) and Hunig's base (0.1 mL, 0.75 mmol, 3 eq.) in acetonitrile (3 mL). The resulting mixture was heated to 80° C. overnight. The reaction mixture was diluted with H2O and extracted with DCM, dried and concentrated to yield (R)-tert-butyl 2-(N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxamido)ethylcarbamate (40 mg, 30%). MS (ESI) m/e (M+H+) 529.

후처리

  1. extractionextracted with DCM
  2. customdried
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f955ff63803b4e68a41305fe2f830ca5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846683B2

연결된 노트

불러오는 중…