2-Chloroacetophenone → HCID 59702117, compound

HRID 902490Notes

Reaction equation

HRID 902490 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[NH:10][C:9]2[CH:13]=[CH:14][S:15][C:8]=2[C:7]=1[N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]2[O:25][CH:26]=[CH:27][CH:28]=2)=[O:23])[CH2:18][CH2:17]1)=[O:5])[CH3:2].Cl[CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:32].C(OC(C1C(=O)N(CC2C=CC(F)=CC=2)C2C=CSC=2C=1N1CCN(C(C2OC=CC=2)=O)CC1)=O)C>>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]([CH2:30][C:31](=[O:32])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:9]2[CH:13]=[CH:14][S:15][C:8]=2[C:7]=1[N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]2[O:25][CH:26]=[CH:27][CH:28]=2)=[O:23])[CH2:18][CH2:17]1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 107572-ChloroacetophenoneHCID 58727588HCID 58727588, compoundHCID 59702060HCID 59702060, compound

Product 1

HCID 59702117HCID 59702117, compound

Procedure

This compound was prepared from 7-[4-(furan-2-carbonyl)-piperazin-1-yl]-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (10) and 2-chloroacetophenone by applying similar method as described for 4-(4-fluoro-benzyl)-7-[4-(furan-2-carbonyl)-piperazin-1-yl]-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (11). MP 246° C. 1H-NMR (DMSO-d6) δ 1.25 (t, J=7.2 Hz, 3H), 3.85 (m, 4H), 4.23 (q, J=6.8 Hz, 2H), 5.75 (s, 2H), 6.66 (m, 1H), 7.07 (d, J=3.2 Hz, 1H), 7.34 (d, J=5.6 Hz, 1H), 7.61 (t, J=7.6 Hz, 2H), 7.73 (t, J=7.6 Hz, 1H), 7.88 (d, J=0.8 Hz, 1H), 8.01 (d, J=5.6 Hz, 1H), 8.10 (d, J=7.6 Hz, 2H); EIMS m/z 520 (M+1).

Sources & evidence

ORD record
ord-521df18acfb44d3183d07ae06bac4570
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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