4-Hydroxypyrrolidine → (7-Chloro-thieno[3,2-b]pyridin-2-yl)-(3-hydroxy-pyrrolidin-1-yl)-methanone

HRID 1063186Notes

Reaction equation

[OH:1][CH:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[CH:14]=[C:15]([C:17]([O-])=[O:18])[S:16][C:9]=12.[Li+]>>[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:17]([C:15]2[S:16][C:9]3[C:10](=[N:11][CH:12]=[CH:13][C:8]=3[Cl:7])[CH:14]=2)=[O:18])[CH2:3]1

Participants

Reactant 2

HCID 982104-Hydroxypyrrolidine

HCID 23677819Lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 22143479(7-Chloro-thieno[3,2-b]pyridin-2-yl)-(3-hydroxy-pyrrolidin-1-yl)-methanone

Procedure

This compound was prepared from (+/−)-3-hydroxypyrrolidine and lithium 7-chloro-thieno[3,2-b]pyridine-2-carboxylate by a procedure analogous to Example 1B. MS: 283/285 (MH+); HPLC Rf: 3.44 min.; HPLC purity 91%.

Sources & evidence

ORD record: ord-7933b80ddd444134b989ab4d3d497337
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06964961B2

Reaction notes

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