Triethylamine → HCID 67056740, compound

HRID 546513Notes

Reaction equation

HRID 546513 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O.C(N(CC)CC)C.Cl.[Cl:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33]([C:38]([NH:40][C@@H:41]1[CH2:46][CH2:45][CH2:44][CH2:43][C@@H:42]1[NH2:47])=[O:39])=[CH:32]2>ClCCl>[ClH:18].[Cl:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33]([C:38]([NH:40][C@@H:41]1[CH2:46][CH2:45][CH2:44][CH2:43][C@@H:42]1[NH:47][C:13]([CH:10]1[CH2:9][CH2:8][N:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH2:12][CH2:11]1)=[O:15])=[O:39])=[CH:32]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 12682891-(Pyridin-4-yl)piperidine-4-carboxylic acidHCID 18442849HCID 18442849, compound

Product 1

HCID 67056740HCID 67056740, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Pyridyl)piperidine-4-carboxylic acid (Tetrahedron, 1998, Vol. 44, p. 7095) (206 mg) was suspended in dichloromethane (50 ml), thionyl chloride (144 μl) was added under ice cooling, and the mixture was stirred for 30 minutes. After triethylamine (969 μl) was added to the reaction mixture, (±)-cis-N-[(5-chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride (328 mg) was added, and the mixture was stirred at room temperature for 30 minutes. After the reaction mixture was concentrated under reduced pressure, and water was added to the residue, the solution was concentrated under reduced pressure, and precipitate deposited was collected by filtration to obtain the title compound (310 mg) as a pale brown solid.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. concentrationthe solution was concentrated under reduced pressure, and precipitate
  6. filtrationdeposited was collected by filtration

Sources & evidence

ORD record
ord-392e4b6d9b5f4856bf4b0ebc5342ec07
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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