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

HRID 1844364Notes

Reaction equation

HRID 1844364 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-21df8ac0907145298d831dd89a3607e5
Source dataset
uspto-grants-2015_02
Patent number
US08946415B2

Reaction notes

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