Triethylamine → HCID 178441265, 화합물

HRID 1888687노트

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HRID 1888687 반응식
CCN=C=NC[CH2:7][CH2:8][N:9]([CH3:11])C.Cl.[CH2:13]([C:17]1=[CH:18][N:19]([C:36]([CH3:39])([CH3:38])[CH3:37])[S:20]/[C:21]/1=[N:22]\[C:23]([C@:25]1([CH3:35])[CH2:29][CH2:28][C@H:27]([C:30]([OH:32])=O)[C:26]1([CH3:34])[CH3:33])=[O:24])[CH2:14][CH2:15][CH3:16].OC1C2N=NNC=2C=CC=1.Cl.N1CCC1.C(N(CC)CC)C>C(OCC)(=O)C.O.CN(C)C=O>[N:9]1([C:30]([C@H:27]2[CH2:28][CH2:29][C@@:25]([CH3:35])([C:23](/[N:22]=[C:21]3/[C:17]([CH2:13][CH2:14][CH2:15][CH3:16])=[CH:18][N:19]([C:36]([CH3:38])([CH3:37])[CH3:39])[S:20]/3)=[O:24])[C:26]2([CH3:33])[CH3:34])=[O:32])[CH2:8][CH2:7][CH2:11]1

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12308726Azetidine hydrochlorideHCID 178418300HCID 178418300, 화합물HCID 178441278HCID 178441278, 화합물

생성물 1

HCID 178441265HCID 178441265, 화합물수율 58.1%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Solid N-(3-dimethylaminopropyl)-n′-ethylcarbodiimide hydrochloride (EDC) (Aldrich, 216 mg, 1.12 mmol), the product from Example 173 (296 mg, 0.750 mmol), hydroxybenzotriazole (Aldrich, 152 mg, 1.12 mmol), azetidine hydrochloride (Aldrich, 105 mg, 1.12 mmol), triethylamine (Aldrich, 152 mg, 1.50 mmol) and anhydrous N,N-dimethylformamide (4 mL) were mixed together at room temperature. Water was added to quench and the mixture was extracted with dichloromethane. The extracts were dried over sodium sulfate and concentrated by rotary evaporator to give a brown oil. Flash chromatography (silica gel: 20-75% ethyl acetate in hexanes) afforded 189 mg (58%) of the title compound. 1H NMR (DMSO-d6) δ 0.50 (s, 3H), 0.90 (t, J=7.8 Hz, 3H), 1.22 (s, 3H), 1.23 (s, 3H), 1.23-1.35 (m, 4H), 1.37-1.46 (m, 1H), 1.56 (s, 9H), 1.56-1.67 (m, 2H), 1.90-2.03 (m, 1H), 2.08-2.22 (m, 2H), 2.71-2.76 (m, 2H), 2.77-2.83 (m, 1H), 3.73-3.81 (m, 1H), 3.82-3.91 (m, 1H), 4.06-4.14 (m, 1H), 4.18-4.26 (m, 1H), 8.50 (s, 1H). MS (ESI+) m/z 434 (M+H)+. Anal. calcd. for C24H39N3O2S: C, 66.47; H, 9.06; N, 9.69. Found: C, 66.60; H, 9.02; N, 9.47.

후처리

  1. customto quench
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe extracts were dried over sodium sulfate
  4. concentrationconcentrated by rotary evaporator
  5. customto give a brown oil

출처 및 근거

ORD 기록
ord-c999a571b3d54a32a6b4c64fe46af011
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501794B2

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