Sulfamide → 7-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid amide

HRID 589943Notes

Reaction equation

HRID 589943 reaction equation
[CH2:1]1[C:3]2([CH2:8][N:7]([C:9]3[C:10]4[CH:17]=[CH:16][NH:15][C:11]=4[N:12]=[CH:13][N:14]=3)[CH2:6][CH2:5][NH:4]2)[CH2:2]1.[S:18](N)([NH2:21])(=[O:20])=[O:19]>O1CCOCC1>[N:12]1[C:11]2[NH:15][CH:16]=[CH:17][C:10]=2[C:9]([N:7]2[CH2:8][C:3]3([CH2:1][CH2:2]3)[N:4]([S:18]([NH2:21])(=[O:20])=[O:19])[CH2:5][CH2:6]2)=[N:14][CH:13]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 668882444-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine2×

Product 1

HCID 574100947-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 4-(4,7-diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine (1 g, 4.4 mmol) (intermediate 21) in dry dioxane (20 mL) was added sulfamide (419 mg, 4.4 mmol). The reaction mixture was heated to reflux for 6 hours. After evaporation of the solvent in vacuo the crude mixture was purified by flash chromatography on silica using heptane→EtOAc:MeOH (9:1) as eluent.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. customAfter evaporation of the solvent in vacuo the crude mixture
  4. customwas purified by flash chromatography on silica

Sources & evidence

ORD record
ord-85e790a9ca824c49a7384c383494e0ac
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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