4-Methylmorpholine → HCID 15951139, compound

HRID 1676958Notes

Reaction equation

HRID 1676958 reaction equation
Cl.[C:2]1([CH2:8][S:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](N3CCC[C@H]3CN3CCCC3)=[O:20])=[CH:15][CH:14]=2)(=[O:11])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4]C=1.C(Cl)(=O)C(Cl)=O.CN1CCOCC1.[NH:45]1[CH2:49][CH2:48][CH2:47][C@H:46]1[CH2:50][N:51]1[CH2:55][CH2:54][CH2:53][CH2:52]1>CN(C)C=O.ClCCl.C(#N)C>[CH3:8][S:9]([C:6]1[CH:5]=[CH:4][C:8]([S:9]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]([N:45]3[CH2:49][CH2:48][CH2:47][C@H:46]3[CH2:50][N:51]3[CH2:55][CH2:54][CH2:53][CH2:52]3)=[O:20])=[CH:17][CH:18]=2)(=[O:10])=[O:11])=[CH:2][CH:7]=1)(=[O:11])=[O:10]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 65578Oxalyl chlorideHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 15951137HCID 15951137, compound

Product 1

HCID 15951139HCID 15951139, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

The title compound is prepared substantially in accordance with the procedure for the free base of C-Phenyl-N-[4-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-phenyl]-methanesulfonamide hydrochloride (Example 21) using the title compound of Intermediate 8 (4-(4-methanesulfonyl-benzenesulfonylamino)-benzoic acid) (0.270 g, 0.761 mmol), oxalyl chloride (0.145 g, 1.14 mmol), 1 drop N,N-dimethylformamide, N-methylmorpholine (0.081 g, 0.8 mmol), and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (0.115 g, 0.75 mmol) in a 1:1 mixture of dichloromethane/acetonitrile. The reaction is purified by radial chromatography to provide 0.338 g (90%) of the title compound as a white solid. MS (ES+) m/e 492.1 (M+1)+.

Workup

  1. customThe reaction is purified by radial chromatography

Sources & evidence

ORD record
ord-92787447e11a40d3b9c42b9f0475974e
Source dataset
uspto-grants-2011_08
Patent number
US08008296B2

Reaction notes

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