Triethylamine → HCID 178441265, compound

HRID 1888687Notes

Reaction equation

HRID 1888687 reaction equation
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

Participants

9

Reactant 5

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

Product 1

HCID 178441265HCID 178441265, compoundYield 58.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c999a571b3d54a32a6b4c64fe46af011
Source dataset
uspto-grants-2013_08
Patent number
US08501794B2

Reaction notes

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