Cesium carbonate → HCID 86706433, compound

HRID 589974Notes

Reaction equation

HRID 589974 reaction equation
C(OC([N:8]1[C:12]2[N:13]=[CH:14][N:15]=[C:16]([N:17]3[CH2:24][C:21]4([CH2:23][CH2:22]4)[N:20]([S:25](=[O:33])(=[O:32])[NH:26][CH2:27][CH2:28][CH2:29][C:30]#[N:31])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=O)(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:41][CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CC#N>[C:30]([CH2:29][CH2:28][CH2:27][N:26]([CH2:41][CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[S:25]([N:20]1[CH2:19][CH2:18][N:17]([C:16]2[C:11]3[CH:10]=[CH:9][NH:8][C:12]=3[N:13]=[CH:14][N:15]=2)[CH2:24][C:21]21[CH2:23][CH2:22]2)(=[O:32])=[O:33])#[N:31]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12503(3-Bromopropyl)benzene2×HCID 68296099HCID 68296099, compound2×

Product 1

HCID 86706433HCID 86706433, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-[4-(3-Cyano-propylsulfamoyl)-4,7-diaza-spiro[2.5]oct-7-yl]-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (intermediate 18) was dissolved in CH3CN (0.4 mL), added Cs2CO3 and (3-bromo-propyl)-benzene. Stirred at for 16 h and then added additional (3-bromo-propyl)-benzene (2 equivalents) before being stirred at rt for 3 days. The crude reaction mixture was filtered through a syringe filter (0.45 μm) and purified by standard preparative HPLC purification. The residual oil was dissolved in THF (1 mL), added TFA (0.5 mL) and then stirred at rt for 2 h. The crude reaction mixture was concentrated in vacuo and redissolved in MeOH (0.5 mL). The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.

Workup

  1. stirringbefore being stirred at rt for 3 days
  2. customThe crude reaction mixture
  3. filtrationwas filtered through a syringe
  4. filtrationfilter (0.45 μm)
  5. custompurified by standard preparative HPLC purification
  6. dissolutionThe residual oil was dissolved in THF (1 mL)
  7. additionadded TFA (0.5 mL)
  8. stirringstirred at rt for 2 h
  9. customThe crude reaction mixture
  10. concentrationwas concentrated in vacuo
  11. dissolutionredissolved in MeOH (0.5 mL)
  12. customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture

Sources & evidence

ORD record
ord-f4eaa7d1de6e4a8f9195a801020917a6
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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