Cesium carbonate → 7-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid phenethyl-(3-phenyl-propyl)-amide

HRID 589969Notes

Reaction equation

HRID 589969 reaction equation
[CH2:1]([NH:9][S:10]([N:13]1[CH2:20][CH2:19][N:18]([C:21]2[C:22]3[CH:29]=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=2)[CH2:17][C:14]21[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C=O)C>[CH2:1]([N:9]([CH2:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[S:10]([N:13]1[CH2:20][CH2:19][N:18]([C:21]2[C:22]3[CH:29]=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=2)[CH2:17][C:14]21[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12503(3-Bromopropyl)benzeneHCID 574100967-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid phenethyl-amide2×

Product 1

HCID 574103197-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid phenethyl-(3-phenyl-propyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid phenethyl-amide (intermediate 5) (0.05 mmol) was dissolved in dry DMF (0.5 mL) and added Cs2CO3 (0.05 mmol) and (3-bromo-propyl)-benzene (0.05 mmol). Stirred at rt for 2 h and then filtered through a syringe filter (0.45 μm). The pure compounds were obtained by standard preparative HPLC purification of the reaction mixture.

Workup

  1. filtrationfiltered through a syringe
  2. filtrationfilter (0.45 μm)
  3. customThe pure compounds were obtained by standard preparative HPLC purification of the reaction mixture

Sources & evidence

ORD record
ord-f1eba224659c41b48cd55ca06b52600f
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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