Diisopropylethylamine → HCID 178457831, 화합물

HRID 518644

반응식

HRID 518644 반응식
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[Cl:24][C:25]1[CH:30]=[C:29](Cl)[C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=1>C(#N)C.O>[Cl:24][C:25]1[CH:30]=[C:29]([NH:2][C@@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]2)[C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 122757652,4-Dichloro-5-nitropyridineHCID 178457872HCID 178457872, 화합물

생성물 1

HCID 178457831HCID 178457831, 화합물수율 73.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a solution of cis-4-amino-N-isopropylcyclohexanecarboxamide hydrochloride (12.58 g, 57.0 mmol) and DIPEA (29.0 mL, 166 mmol) in ACN (104 mL) was added 2,4-dichloro-5-nitropyridine (10.00 g, 51.8 mmol). The resulting mixture was stirred at RT for 24 hours. The reaction mixture was diluted with water and washed with DCM (×2). The combined organic layers were washed with a minimal volume of brine, dried over sodium sulfate, filtered and concentrated in vacuo. After almost complete concentration of solvent, EtOAc was added, and the solid precipitate was collected yielding cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide as a yellow solid (12.97 g, 73.4% yield).

후처리

  1. washwashed with DCM (×2)
  2. washThe combined organic layers were washed with a minimal volume of brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. concentrationAfter almost complete concentration of solvent, EtOAc
  7. additionwas added
  8. customthe solid precipitate was collected

출처 및 근거

ORD 기록
ord-a2f0400b1f944df0b7ffa6e47a56d027
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115127B2

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