1-Hydroxybenzotriazole → (2(S)-Pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-(4-thiophen-2-yl-phenyl)-methanone

HRID 646414Notes

Reaction equation

HRID 646414 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:46]1[CH2:50][CH2:49][CH2:48][C@H:47]1[CH2:51][N:52]1[CH2:56][CH2:55][CH2:54][CH2:53]1>CN(C=O)C.ClCCl>[N:52]1([CH2:51][C@@H:47]2[CH2:48][CH2:49][CH2:50][N:46]2[C:10]([C:9]2[CH:8]=[CH:7][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[CH:14][CH:13]=2)=[O:12])[CH2:56][CH2:55][CH2:54][CH2:53]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7364984-(Thiophen-2-yl)benzoic acidHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 11493848(2(S)-Pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-(4-thiophen-2-yl-phenyl)-methanoneYield 35%

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 10 mL 10% DMF/dichloromethane using 4-(thiophen-2-yl)-benzoic acid (CAS 29886-62-2) (182 mg, 0.89 mmol), EDC-HCl (254 mg, 1.33 mmol), HOBt (180 mg, 1.33 mmol), DIEA (0.39 mL, 2.22 mmol) and (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (116 mg, 10.0 mmol) to give the title compound (90 mg, 35% yield). MS (ES+) 341.2 (M+H)+

Sources & evidence

ORD record
ord-412dbde9c74e4402a52a25f6dc0f6adc
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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