N-cyclobutylsulfamoyl chloride → N-cyclobutyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

HRID 589954Notes

Reaction equation

HRID 589954 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.[CH:18]1([NH:22][S:23](Cl)(=[O:25])=[O:24])[CH2:21][CH2:20][CH2:19]1>N1C=CC=CC=1>[CH:18]1([NH:22][S:23]([N:4]2[C:3]3([CH2:1][CH2:2]3)[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]2)(=[O:25])=[O:24])[CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 22326606N-cyclobutylsulfamoyl chloride2×HCID 668882444-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine2×

Product 1

HCID 68296040N-cyclobutyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 4-(4,7-diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine (6.55 mmol) (intermediate 21) in dry pyridine (25 mL) was added N-cyclobutylsulfamoyl chloride (7.86 mmol) (Intermediate 29). The reaction mixture was stirred at rt for 16 h. After evaporation of the solvent in vacuo the crude mixture was purified by flash chromatography on silica using heptane→MeOH:EtOAc affording the title compound as white crystals.

Workup

  1. customAfter evaporation of the solvent in vacuo the crude mixture
  2. customwas purified by flash chromatography on silica

Sources & evidence

ORD record
ord-3ad250eda9284e499d0391207959766a
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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