Cesium carbonate → HCID 69328078, compound

HRID 902487Notes

Reaction equation

HRID 902487 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:29]([O-])([O-])=O.[Cs+].[Cs+].Cl.ClC[C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1>CN1C(=O)CCC1>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]([C:38]2[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=2)[C:9]2[CH:13]=[C:14]([CH3:29])[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 10796Cesium carbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 59702095HCID 59702095, compound

Product 1

HCID 69328078HCID 69328078, 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) (856 mg, 2.05 mmol), Cs2CO3 (2.75 g, 8.4 mmol), 3-chloromethyl pyridine hydrochloride (0.370 g, 2.25 mmol) and KI (1 g) 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. 1H-NMR (DMSO-d6) δ 3.13 (t, J=7.2 Hz, 3H), 3.80 (m, 4H), 4.27 (q, J=7.2 Hz, 2H), 5.40 (s, 2H), 7.15 (m, 1H), 7.35 (m, 1H), 7.44 (d, J=6.0 Hz, 1H), 7.48 (dd, J=1.2, 3.6 Hz, 1H), 7.60 (m, 1H), 7.79 (dd, J=0.8, 4.8 Hz, 1H), 8.06 (d, J=5.6 Hz, 1H), 8.47 (dd, J=1.6, 4.8 Hz, 1H), 8.56 (d, J=1.6 Hz, 1H); EIMS m/z 509 (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-ac51aa2c154e47ef937b52824a72c2c8
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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