7-Benzyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile → 7-Benzyl-3-methyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile

HRID 902530Notes

Reaction equation

HRID 902530 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]#[N:16])=[C:11](Cl)[C:10]2[C:18]([CH3:21])=[CH:19][S:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C(=O)C(C#N)=C([N:38]2[CH2:43][CH2:42][N:41]([C:44]([C:46]3[S:47][CH:48]=[CH:49][CH:50]=3)=[O:45])[CH2:40][CH2:39]2)C2C=CSC1=2)C1C=CC=CC=1>>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]#[N:16])=[C:11]([N:38]2[CH2:43][CH2:42][N:41]([C:44]([C:46]3[S:47][CH:48]=[CH:49][CH:50]=3)=[O:45])[CH2:40][CH2:39]2)[C:10]2[C:18]([CH3:21])=[CH:19][S:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 118526987-Benzyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrileHCID 597020577-Benzyl-4-chloro-6,7-dihydro-3-methyl-6-oxo-thieno[2,3-b]pyridine-5-carbonitrile

Product 1

HCID 597020767-Benzyl-3-methyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrileYield 25%

Procedure

This compound was prepared from 7-benzyl-4-chloro-6,7-dihydro-3-methyl-6-oxo-thieno[2,3-b]pyrdine-5-carbonitrile (65) by applying the same method as described for the preparation of 7-benzyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (66). Yield 25%; MP 223° C. 1H-NMR (DMSO-d6) δ 2.48 (d, J=0.8 Hz, 3H), 3.50 (m, 4H), 3.86 (b, 4H), 5.30 (s, 2H), 6.99 (d, J=1.2 Hz, 1H), 7.16 (m, 1H), 7.30 (m, 5H), 7.47 (dd, J=0.8, 3.6 Hz, 1H), 7.80 (dd, J=1.2, 5.2 Hz, 1H) ppm; EIMS m/z 475 (M+1).

Sources & evidence

ORD record
ord-67fa71651fd541b2bff14938e71a750f
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

Loading…