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

HRID 589945ノート

反応式

HRID 589945 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 3283Diethyl Ether溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2b23776148884c8f8acab196555226c8
出典データセット
uspto-grants-2016_01
特許番号
US09233964B2

反応ノート

読み込み中…