Diisopropylethylamine → 2-(1H-Benzo[d]imidazol-1-yl)-N-((R)-8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine

HRID 605868노트

반응식

HRID 605868 반응식
F[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1OCC[C@H]2N.Cl[C:14]1[N:19]=C(Cl)C([N+]([O-])=O)=C[N:15]=1.CCN(C(C)C)C(C)C.Cl[C:34]1[N:39]=[C:38]([NH:40][C@H:41]2[C:50]3[C:45](=[C:46]([F:51])[CH:47]=[CH:48][CH:49]=3)[O:44][CH2:43][CH2:42]2)[C:37]([N+:52]([O-:54])=[O:53])=[CH:36][N:35]=1>C1COCC1>[N:15]1([C:34]2[N:39]=[C:38]([NH:40][C@H:41]3[C:50]4[C:45](=[C:46]([F:51])[CH:47]=[CH:48][CH:49]=4)[O:44][CH2:43][CH2:42]3)[C:37]([N+:52]([O-:54])=[O:53])=[CH:36][N:35]=2)[C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][C:11]=2[N:19]=[CH:14]1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 46911919(R)-8-fluorochroman-4-amineHCID 59704905(R)-2-chloro-N-(8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine

생성물 1

HCID 597049352-(1H-Benzo[d]imidazol-1-yl)-N-((R)-8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

(R)-8-Fluorochroman-4-amine (60 mg) was added to a solution of 2,4-dichloro-5-nitropyrimidine (70 mg) and DIEA (0.14 mL) in THF (5 mL) at −78° C. The reaction mixture was stirred for a further 15 min at −78° C. then removed from the cold bath and allowed to warm to RT. A one molar solution of the sodium salt of benzimidazole (0.7 ml, stock solution prepared via the addition of sodium hydride to a benzimidazole solution in THF) was added to the reaction intermediate ((R)-2-chloro-N-(8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine) and the resulting mixture was stirred at RT overnight. Purification via column chromatography (elution with MeOH/DCM) gave the titled compound (120 mg), MH+=407.

후처리

  1. customthen removed from the cold bath
  2. temperatureto warm to RT
  3. customA one molar solution of the sodium salt of benzimidazole (0.7 ml, stock solution prepared via the addition of sodium hydride to a benzimidazole solution in THF)
  4. stirringthe resulting mixture was stirred at RT overnight
  5. customPurification
  6. washvia column chromatography (elution with MeOH/DCM)

출처 및 근거

ORD 기록
ord-ebdd6726f1c54ef0b61f0ec2bd91efa8
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915268B2

반응 노트

불러오는 중…