Water → HCID 57410093, compound

HRID 589964Notes

Reaction equation

HRID 589964 reaction equation
[C:1]([O:5][C:6]([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:36])(=[O:35])[NH:26][CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:44][CH3:45].O>CN(C=O)C>[C:1]([O:5][C:6]([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:35])(=[O:36])[N:26]([CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:2][CH2:1][CH2:3][C:45]4[CH:44]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 10796Cesium carbonateHCID 68295913HCID 68295913, compound2×

Product 1

HCID 57410093HCID 57410093, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Phenethylsulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (intermediate 6) (0.1 mmol) was dissolved in dry DMF (0.5 mL) and added Cs2CO3 (0.12 mmol) and bromo-ethane (0.12 mmol). Stirred at rt for 16 h and then added H2O (2 mL). Extracted with EtOAc (3×2 mL) and the combined organic phases were concentrated in vacuo. The residual oil was treated with TFA (1 mL) at rt for 3 h. The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.

Workup

  1. extractionExtracted with EtOAc (3×2 mL)
  2. concentrationthe combined organic phases were concentrated in vacuo
  3. additionThe residual oil was treated with TFA (1 mL) at rt for 3 h
  4. customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture

Sources & evidence

ORD record
ord-6724b68ea6e74054a6a20a47261f8b4b
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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