Dimethylformamide → (S)-2-amino-1-(4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)-3-methylbutan-1-one

HRID 1478284노트

반응식

HRID 1478284 반응식
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][C:6]=12.CN(C(ON1N=NC2[CH:28]=[CH:29][CH:30]=[N:31]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:41](N(CC)CC)C.CN([CH:51]=[O:52])C>C(Cl)Cl>[NH2:31][C@@H:30]([CH:29]([CH3:41])[CH3:28])[C:51]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[CH:9]=[CH:10][N:5]3[N:4]=[CH:3][C:2]([Br:1])=[C:6]3[N:7]=2)[CH2:12][CH2:13]1)=[O:52]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866974343-Bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine

생성물 1

HCID 86697450(S)-2-amino-1-(4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)-3-methylbutan-1-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine (400 mg, 1.42 mmol) Boc-L-Leucine (392 mg, 1.7 mmol), HATU (490 mg, 2.13 mmol), and triethylamine (788 uL, 5.7 mmol) taken up in DMF and stirred at room temperature overnight. Reaction diluted with DCM washed with water, DCM layer then dried over magnesium sulfate filtered and reduced in Vacuo. This was then taken up in 26 mL DCM and 4 mL TFA added. Stirred 1 hour until complete by LC/MS. Reaction was washed with 1N NaOH, DCM layer removed dried over magnesium sulfate filtered, reduced in vacuo to obtain 349 mg crude product for further reaction as is. LRMS (ESI) m/z 381/383 [(M+H)]+, calc'd for C15H21BrN6O: 381.28.

후처리

  1. customReaction
  2. washwashed with water, DCM layer
  3. dry with materialthen dried over magnesium sulfate
  4. filtrationfiltered
  5. addition4 mL TFA added
  6. stirringStirred 1 hour until complete by LC/MS
  7. customReaction
  8. washwas washed with 1N NaOH, DCM layer
  9. customremoved
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered

출처 및 근거

ORD 기록
ord-8290046fd63a4c2aae5d8b9deae79375
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403832B2

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