Cesium carbonate → HCID 59702060, compound

HRID 902488Notes

Reaction equation

HRID 902488 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].C([O-])([O-])=O.[Cs+].[Cs+].[F:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1>CN1C(=O)CCC1>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]([CH2:40][C:39]2[CH:42]=[CH:43][C:36]([F:35])=[CH:37][CH:38]=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

5

Reactant 3

HCID 10796Cesium carbonateHCID 680214-Fluorobenzyl bromideHCID 58727588HCID 58727588, compound

Product 1

HCID 59702060HCID 59702060, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 7-[4-(furan-2-carbonyl)-piperazin-1-yl]-5-oxo-4,5-dihydro-thieno[3,2-b]pyrdine-6-carboxylic acid ethyl ester (10) (750 mg, 1.87 mmol), Cs2CO3 (1.83 g, 5.63 mmol), 4-fluoro benzyl bromide (0.276 mL, 2.24 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 reverse phase flash chromatography in combiflash eluting with water/acetonitrile gradient. Yield 240 mg (25%). 1H-NMR (DMSO-d6) δ 1.27 (t, J=6.8 Hz, 3H), 3.36 (m, 4H), 3.82 (m, 4H), 4.26 (q, J=6.8 Hz, 2H), 5.35 (s, 2H), 6.65 (m, 1H), 7.06 (dd, J=0.8, 3.6 Hz, 1H), 7.16 (m, 2H), 7.32 (m, 3H), 7.87 (m, 1H), 8.03 (d, J=5.6 Hz, 1H); EIMS m/z 510 (M+1).

Workup

  1. customthe solids formed
  2. filtrationwere filtered
  3. washwashed by cold water
  4. customdried
  5. customThe crude product was purified by reverse phase flash chromatography in combiflash
  6. washeluting with water/acetonitrile gradient

Sources & evidence

ORD record
ord-cc7dda4b640143aa95b36b76883e4bd5
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

Loading…