Pyrrolidine → (R)-(7-Chlorothieno[3,2-b]pyridin-2-yl)(3-(dimethylamino)pyrrolidin-1-yl)methanone

HRID 2193657Notes

Reaction equation

HRID 2193657 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[O:12])[S:10][C:3]=12.[NH:18]1[CH2:22]CC[CH2:19]1.CN(C)[C@@H]1CCNC1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][C@@H:15]([N:18]([CH3:22])[CH3:19])[CH2:14]3)=[O:12])[S:10][C:3]=12

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 11173165(7-Chlorothieno[3,2-b]pyridin-2-yl)(pyrrolidin-1-yl)methanone

Product 1

HCID 20745989(R)-(7-Chlorothieno[3,2-b]pyridin-2-yl)(3-(dimethylamino)pyrrolidin-1-yl)methanone

Procedure

Following the procedures described above for the compound 21 (example 5f, steps 1-3) but substituting pyrrolidine in the step 3 for (R)—N,N-dimethylpyrrolidin-3-amine, title compound 24 was obtained as a white solid (58% yield). MS (m/z): 310.0 (M+H).

Sources & evidence

ORD record
ord-1401c9136a4d495398ea4e731755db65
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

Loading…