2-Chloroacetophenone → HCID 59702107, compound

HRID 902486Notes

Reaction equation

HRID 902486 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[S:25][CH:26]=[CH:27][CH:28]=2)=[O:23])[CH2:18][CH2:17]1)=[O:5])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:36][C:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:38]>CN1C(=O)CCC1>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]([CH2:36][C:37](=[O:38])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=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[S:25][CH:26]=[CH:27][CH:28]=2)=[O:23])[CH2:18][CH2:17]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 107572-ChloroacetophenoneHCID 10796Cesium carbonateHCID 59702095HCID 59702095, compound

Product 1

HCID 59702107HCID 59702107, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (5) (750 mg, 1.79 mmol), Cs2CO3 (1.76 g, 5.40 mmol), 2-chloroacetophenone (0.333 g, 2.15 mmol) in dry NMP was heated overnight at 90° C. The solution was poured into ice water and the solids formed were filtered, washed by cold water, and dried. The crude product was purified by recrystallization with acetone. MP 240° C. 1H-NMR (DMSO-d6) δ 1.26 (t, J=7.2 Hz, 3H), 3.39 (m, 4H), 3.83 (m, 4H), 4.23 (q, J=7.2 Hz, 2H), 4.23 (q, J=7.2 Hz, 2H), 5.75 (s, 2H), 7.16 (m, 1H), 7.34 (d, J=5.6 Hz, 1H), 7.50 (dd, J=1.2, 3.6 Hz, 1H), 7.61 (t, J=7.6 Hz, 2H), 7.74 (m, 1H), 7.80 (dd, J=1.2, 5.2 Hz, 1H), 8.01 (d, J=7.0 Hz, 1H), 8.10 (m, 2H); EIMS m/z 536(M+1).

Workup

  1. customthe solids formed
  2. filtrationwere filtered
  3. washwashed by cold water
  4. customdried
  5. customThe crude product was purified by recrystallization with acetone

Sources & evidence

ORD record
ord-1919407ccbf34c8abbadff148b727f20
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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