(S)-(+)-2-(Anilinomethyl)pyrrolidine → HCID 67492439, compound

HRID 1921441Notes

Reaction equation

HRID 1921441 reaction equation
[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[S:15][C:14]([S:16]([Cl:19])(=[O:18])=[O:17])=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2].[C:20]1([NH:26][CH2:27][C@@H:28]2[CH2:32][CH2:31][CH2:30][NH:29]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[ClH:19].[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[S:15][C:14]([S:16]([N:29]3[CH2:30][CH2:31][CH2:32][C@H:28]3[CH2:27][NH:26][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:18])=[O:17])=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6950385(S)-(+)-2-(Anilinomethyl)pyrrolidineHCID 866103525-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride

Product 1

HCID 67492439HCID 67492439, compoundYield 77%

Procedure

5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride is reacted with (S)-phenyl-pyrrolidin-2-ylmethyl-amine as described in Steps 5 and 6, Example 24 to give the title compound as a yellow glass (77% yield). LC/MS: RT 3.29 min, m/e 458 (M+H); 1H NMR (δ, ppm): 11.84 (1H, s), 7.65 (1H, d), 7.35 (1H, s), 7.25 (1H, d), 7.14 (2H, t), 6.74 (2H, d), 6.62 (1H, t), 3.76 (1H, m), 3.34-3.45 (2H, m), 3.06-3.20 (2H, m), 2.39 (2H, q), 2.30 (3H, s), 1.86 (2H, m), 1.51-1.58 (2H, m), 1.09 (3H, t).

Sources & evidence

ORD record
ord-32643af3ee774638b9094e93cdb5853e
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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