Formaldehyde → 6-[4-((R)-3-Dimethylaminopyrrolidin-1-yl)phenyl]-2-p-tolyl-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one

HRID 69425Notes

Reaction equation

HRID 69425 reaction equation
CC1C=C(C2C=CC(C)=CC=2)SC=1C(O)=O.C=O.S(Cl)(Cl)=O.Cl[CH2:24][CH2:25][C:26]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)[S:28][C:27]=1[C:38](Cl)=[O:39].[NH2:41][C:42]1[CH:47]=[CH:46][C:45]([N:48]2[CH2:52][CH2:51][C@@H:50]([N:53]([CH3:55])[CH3:54])[CH2:49]2)=[CH:44][CH:43]=1>>[CH3:54][N:53]([CH3:55])[C@@H:50]1[CH2:51][CH2:52][N:48]([C:45]2[CH:46]=[CH:47][C:42]([N:41]3[CH2:24][CH2:25][C:26]4[CH:30]=[C:29]([C:31]5[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=5)[S:28][C:27]=4[C:38]3=[O:39])=[CH:43][CH:44]=2)[CH2:49]1

Participants

6

Reactant 5

HCID 712FormaldehydeHCID 24386Thionyl ChlorideHCID 59815627[(R)-1-(4-aminophenyl)pyrrolidin-3-yl]dimethylamineHCID 668791043-Methyl-5-p-tolylthiophene-2-carboxylic acidHCID 866351043-(2-Chloroethyl)-5-p-tolylthiophene-2-carbonyl chloride

Product 1

HCID 579168236-[4-((R)-3-Dimethylaminopyrrolidin-1-yl)phenyl]-2-p-tolyl-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one

Procedure

Firstly 3-methyl-5-p-tolylthiophene-2-carboxylic acid was reacted with paraformaldehyde by method C1, and then the product was treated with thionyl chloride by method B. The resulting 3-(2-chloroethyl)-5-p-tolylthiophene-2-carbonyl chloride was finally reacted with [(R)-1-(4-aminophenyl)pyrrolidin-3-yl]dimethylamine by method A. The product with the molecular weight of 431.60 (C26H29N3OS) was obtained in this way; MS (ESI): 432 (M+H+).

Workup

  1. customThe product with the molecular weight of 431.60 (C26H29N3OS) was obtained in this way

Sources & evidence

ORD record
ord-f20ab9a191504311b944c1998039241c
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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