Thiomorpholine → HCID 54312048, compound

HRID 2288184Notes

Reaction equation

HRID 2288184 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15](O)=[O:16])[CH2:10][C@H:9]1[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=[O:7].[NH:37]1[CH2:42][CH2:41][S:40][CH2:39][CH2:38]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:33][C:31]([F:34])([F:32])[C:29]1[CH:28]=[C:5]([CH:4]=[C:3]([C:2]([F:36])([F:35])[F:1])[CH:30]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([N:37]2[CH2:42][CH2:41][S:40][CH2:39][CH2:38]2)=[O:16])[CH2:10][C@H:9]1[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=[O:7]

Participants

7

Reactant 5

HCID 67164ThiomorpholineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10962313HCID 10962313, compound

Product 1

HCID 54312048HCID 54312048, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(carboxymethyl)-2-(1H-indol-3-ylmethyl)piperazine (0.4 g) and thiomorpholine (0.08 g) in dry N,N-dimethylformamide (4 ml) were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.16 g) and 1-hydroxybenzotriazole (0.12 g) at room temperature. After 3 hours, the reaction mixture was poured into aqueous sodium bicarbonate solution (40 ml) and the resulting precipitate was collected by filtration. The crude product obtained was purified by column chromatography on silica gel using toluene-ethyl acetate (1:2) as an eluent to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(thiomorpholinocarbonylmethyl)piperazine (0.42 g).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customThe crude product obtained
  3. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-82e6a7f23acf4061a228ca9633d21445
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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