Triethylamine → HCID 22632472, compound

HRID 2417537Notes

Reaction equation

HRID 2417537 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]([CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:10](=[O:27])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.CS[C:32]1[NH:33][CH2:34][CH2:35][N:36]=1.C(N(CC)CC)C>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]([CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([C:32]4[NH:36][CH2:35][CH2:34][N:33]=4)[CH2:23][CH2:22]3)[C:10](=[O:27])[CH2:9]2)=[O:7])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 883692-Methylthio-2-imidazoline hydroiodideHCID 22632481HCID 22632481, compound

Product 1

HCID 22632472HCID 22632472, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

30 mg (0.073 mmol) of 4-(4-chlorobenzoyl)-1-[2-(4-piperidinyl)-ethyl]-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on obtained in step 1 in Example 168 and 178 mg (0.73 mmol) of 2-methylthio-2-imidazoline were dissolved in 7 ml of methanol. 0.2 mg (1.4 mmol) of triethylamine was added to the obtained solution, and they were stirred at 70° C. overnight. The solvent was evaporated, and the obtained crude product was treated by the reversed phase high-performance liquid chromatography with silica gel chemically bonded with octadodecyl group as the filler and then eluted with a solvent mixture of water and acetonitrile containing 0.1% (V/V) of trifluoroacetic acid. Acetonitrile was evaporated. After the extraction with dichloromethane, the title compound was obtained.

Workup

  1. customThe solvent was evaporated
  2. customthe obtained crude product
  3. additionwas treated by the reversed phase high-performance liquid chromatography with silica gel
  4. washeluted with a solvent mixture of water and acetonitrile containing 0.1% (V/V) of trifluoroacetic acid
  5. customAcetonitrile was evaporated
  6. extractionAfter the extraction with dichloromethane

Sources & evidence

ORD record
ord-8d1581127fa34d82ac7adb02cd9c1554
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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