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

HRID 589945노트

반응식

HRID 589945 반응식
[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]

참가 물질

6

반응물 3

HCID 962WaterHCID 11789235N-Methylsulfamoyl chloride3회HCID 668882444-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine2회

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 3283Diethyl Ether용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2b23776148884c8f8acab196555226c8
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233964B2

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