Dimethylformamide → HCID 86697447, compound

HRID 1844362Notes

Reaction equation

HRID 1844362 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:15]C[C@H:13](NC)[CH2:12]3)=[N:7][C:6]=12.CN(C(ON1N=N[C:28]2[CH:29]=[CH:30][CH:31]=[N:32]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:42](N(CC)CC)C.[CH3:49][N:50]([CH:52]=[O:53])[CH3:51]>C(Cl)Cl>[NH2:32][C@@H:31]([CH2:30][CH:29]([CH3:42])[CH3:28])[C:52]([N:50]([C@H:51]1[CH2:13][CH2:12][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)[CH2:15]1)[CH3:49])=[O:53]

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 86697448HCID 86697448, compound

Product 1

HCID 86697447HCID 86697447, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-1-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-N-methylpyrrolidin-3-amine (200 mg, 0.68 mmol) Boc-L-Leu (187 mg, 0.81 mmol), HATU (385 mg, 1.01 mmol), and triethylamine (375 uL, 2.7 mmol) Taken up in DMF and Stirred at room temp 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 washed with 1N NaOH, DCM layer removed dried over magnesium sulfate filtered, reduced in vacuo for 226 mg crude product used as is in part D. LRMS (ESI) m/z 409/411 [(M+H)]+, calc'd for C17H24BrN6O: 409.

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. washwashed with 1N NaOH, DCM layer
  9. customremoved
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered

Sources & evidence

ORD record
ord-6f3b625deb20401ba51f539571725569
Source dataset
uspto-grants-2015_02
Patent number
US08946415B2

Reaction notes

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