Cesium carbonate → HCID 53373725, compound

HRID 909266Notes

Reaction equation

HRID 909266 reaction equation
[Br:1][C:2]1[C:3]([S:11][C:12]2[NH:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[C:15]=3[N:21]=2)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.CC1C=CC(S(O[CH2:33][CH2:34][CH:35]2[CH2:40][CH2:39][N:38]([CH:41]=[O:42])[CH2:37][CH2:36]2)(=O)=O)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[NH2:20][C:16]1[C:15]2[N:21]=[C:12]([S:11][C:3]3[C:2]([Br:1])=[CH:10][C:6]4[O:7][CH2:8][O:9][C:5]=4[CH:4]=3)[N:13]([CH2:33][CH2:34][CH:35]3[CH2:40][CH2:39][N:38]([CH:41]=[O:42])[CH2:37][CH2:36]3)[C:14]=2[CH:19]=[CH:18][N:17]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 59581109HCID 59581109, compoundHCID 67145169HCID 67145169, compound

Product 1

HCID 53373725HCID 53373725, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-1H-imidazo[4,5-c]pyridin-4-amine (175 mg, 0.480 mmol), 2-(1-formylpiperidin-4-yl)ethyl 4-methylbenzenesulfonate (194 mg, 0.624 mmol), and Cs2CO3 (267 mg, 0.816 mmol) in DMF (3.0 mL) was heated at 85° C. for 10 h. After cooling to RT, the mixture was diluted with water, extracted with ethyl acetate, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuum. The residue was triturated with EtOAc, filtered, and dried to give the title compound (102 mg, 42%): 1H NMR (DMSO-d6) δ 7.94 (s, 1H), 7.72 (d, J=6.0 Hz, 2H), 7.39 (s, 1H), 6.79 (d, J=6.0 Hz, 2H), 6.66 (s, 1H), 6.41 (s, 2H), 6.07 (s, 2H), 4.20 (t, J=6.8 Hz, 2H), 4.10 (brd, J=13.6 Hz, 1H), 3.62 (brd, J=13.2 Hz, 1H), 2.91 (td, J=12.0, 2.4 Hz, 1H), 2.54 (m, 1H), 1.70 (t, J=6.8 Hz, 2H), 1.57-1.42 (m, 3H), 1.03 (m, 1H), 0.94 (m, 1H); LC/MS [M+H]+ 504.07.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customThe residue was triturated with EtOAc
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-7f31b670df5149a6a3fdd3d6bb8cc54d
Source dataset
uspto-grants-2011_09
Patent number
US08017780B1

Reaction notes

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