Water → 3-bromo-N-(5-cyanopyridin-2-yl)-N-methyl-6,7-dihydropyrazolo-[1,5-a]pyrazine-5(4H)-carboxamide

HRID 539583노트

반응식

HRID 539583 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH3:13])[C:10](Cl)=[O:11])=[N:7][CH:8]=1)#[N:2].[Br:14][C:15]1[CH:16]=[N:17][N:18]2[CH2:23][CH2:22][NH:21][CH2:20][C:19]=12.C(N(CC)CC)C.O>C1COCC1.CN(C)C1C=CN=CC=1>[Br:14][C:15]1[CH:16]=[N:17][N:18]2[CH2:23][CH2:22][N:21]([C:10]([N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=3)[CH3:13])=[O:11])[CH2:20][C:19]=12

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 826585583-bromo-4H,5H,6H,7H-pyrazolo(1,5-a)pyrazineHCID 86720259(5-Cyanopyridin-2-yl)(methyl)carbamic chloride

생성물 1

HCID 867202603-bromo-N-(5-cyanopyridin-2-yl)-N-methyl-6,7-dihydropyrazolo-[1,5-a]pyrazine-5(4H)-carboxamide수율 44%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of (5-cyanopyridin-2-yl)(methyl)carbamic chloride (I-28) in THF (2.0 mL) were added 3-bromo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine (137 mg, 0.680 mmol), triethylamine (0.14 mL, 1.021 mmol) and 4-dimethylaminopyridine (2.0 mg, 0.017 mmol). The mixture was stirred at 60° C. for 1 h. Subsequently, water (25 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The resulting crude product was purified by preparative TLC to afford 60 mg (44%) of 3-bromo-N-(5-cyanopyridin-2-yl)-N-methyl-6,7-dihydropyrazolo-[1,5-a]pyrazine-5(4H)-carboxamide (I-29) as a off white solid. 1H NMR (400 MHz, DMSO) δ 8.64 (s, 1H), 8.07 (d, J=8.8 Hz, 1H), 7.60 (s, 1H), 7.18 (d, J=8.4 Hz, 1H), 4.53 (s, 2H), 4.16 (t, J=4.9 Hz, 2H), 3.84 (t, J=4.9 Hz, 2H), 3.26 (s, 3H); ESI-LC/MS (m/z): [M+H]+ 360.91, [(M+2)+H]+ 362.93, RT 1.63 min.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting crude product was purified by preparative TLC

출처 및 근거

ORD 기록
ord-aba3283e3bf044949c194ea845d48b74
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871754B2

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