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

HRID 418584Notes

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

Reactant 3

HCID 31268Pyrrolidine

HCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidine

HCID 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-aeb803c39b7d4f6c99cec7e7b88c4fc5
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093264B2

Reaction notes

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