1-Hydroxybenzotriazole → [4-(5-Ethanesulfonyl-thiophen-2-yl)-phenyl]-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone

HRID 646423Notes

Reaction equation

HRID 646423 reaction equation
[CH2:1]([S:3]([C:6]1[S:10][C:9]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].[Li].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:52][C@@H:53]1[CH2:57][CH2:56][CH2:55][N:54]1[CH2:58][C@@H:59]1[CH2:63][CH2:62][CH2:61][NH:60]1>CN(C=O)C.ClCCl>[CH2:1]([S:3]([C:6]1[S:10][C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:15]([N:60]3[CH2:61][CH2:62][CH2:63][C@H:59]3[CH2:58][N:54]3[CH2:55][CH2:56][CH2:57][C@H:53]3[CH3:52])=[O:17])=[CH:18][CH:19]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:5])[CH3:2]

Participants

8

Reactant 6

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3028194LithiumHCID 46911921(R)-2-methyl-1-((S)-pyrrolidin-2-ylmethyl)pyrrolidineHCID 59264655HCID 59264655, compound

Product 1

HCID 11619244[4-(5-Ethanesulfonyl-thiophen-2-yl)-phenyl]-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanoneYield 50%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

The title compound is prepared in a manner substantially analogous to General Procedure D in 5 mL 50% DMF/dichloromethane using 4-(5-ethanesulfonyl-thiophen-2-yl)-benzoic acid, Lithium salt (118 mg, 0.39 mmol), EDC-HCl (115 mg, 0.60 mmol), HOBt (81 mg, 0.60 mmol), DIEA (0.17 mL, 1.0 mmol) and 2-(R)-Methyl-1-(2-(S)-pyrrolidinylmethyl)pyrrolidine (61 mg, 0.36 mmol) to give the title compound (80 mg, 50% yield). MS (ES+) 447.3 (M+H)+

Sources & evidence

ORD record
ord-33fc9a92d385406daf1ccc93165162ac
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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