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

HRID 589945Notes

Reaction equation

HRID 589945 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.[CH3:18][NH:19][S:20](Cl)(=[O:22])=[O:21].O>N1C=CC=CC=1.CCOCC>[CH3:18][NH:19][S:20]([N:4]1[CH2:5][CH2:6][N:7]([C:9]2[C:10]3[CH:17]=[CH:16][NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:8][C:3]21[CH2:1][CH2:2]2)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 962WaterHCID 11789235N-Methylsulfamoyl chloride3×HCID 668882444-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine2×

Product 1

HCID 574100957-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid methylamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent3×

Procedure

To 4-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine (2 g, 8.7 mmol) (intermediate 21) in dry pyridine (100 mL) was cooled to 0° C. and dropwise added a solution of commercial available methylsulfamoyl chloride (419 mg, 8.7 mmol) in dry Et2O (5 mL). After complete addition, the reaction mixture was allowed to warm up to rt and was afterwards stirred at rt for 1 h. An additional equivalent of methylsulfamoyl chloride (419 mg, 8.7 mmol) in dry Et2O (5 mL) was added and after additional 1 h at rt a third equivalent of methylsulfamoyl chloride (419 mg, 8.7 mmol) in dry Et2O (5 mL) was added. The crude mixture was treated with water (150 mL) and extracted with EtOAc (3×100 mL). The combined organic phases were washed with H2O (2×50 mL), brine (2×50 mL), dried over Na2SO4, filtered and concentrated in vacuo. Recrystallised in EtOH:CH2Cl2 affording the title compound as white crystals.

Workup

  1. additionAfter complete addition
  2. additionwas added
  3. extractionextracted with EtOAc (3×100 mL)
  4. washThe combined organic phases were washed with H2O (2×50 mL), brine (2×50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customRecrystallised in EtOH

Sources & evidence

ORD record
ord-2b23776148884c8f8acab196555226c8
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

Loading…