Triethylamine → HCID 178429384, compound

HRID 707429Notes

Reaction equation

HRID 707429 reaction equation
[NH2:1][C@@H:2]1[CH2:5][C@H:4]([N:6]2[C:10]3=[N:11][CH:12]=[CH:13][N:14]=[C:9]3[C:8]([CH3:16])([CH3:15])[C:7]2=[O:17])[CH2:3]1.[NH:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[C:27](O)=[O:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl>[CH3:16][C:8]1([CH3:15])[C:9]2[C:10](=[N:11][CH:12]=[CH:13][N:14]=2)[N:6]([C@@H:4]2[CH2:5][C@H:2]([NH:1][C:27]([C:19]3[NH:18][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[N:20]=3)=[O:28])[CH2:3]2)[C:7]1=[O:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2332402-Benzimidazolecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178429367HCID 178429367, compound

Product 1

HCID 178429384HCID 178429384, compoundYield 9.13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a round bottomed flask was added 5-(cis-3-aminocyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (0.1518 g, 0.497 mmol), 1H-benzimidazole-2-carboxylic acid (0.097 g, 0.597 mmol, ChemBridge Corporation), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.246 g, 0.647 mmol, GenScript) and triethylamine (0.277 ml, 1.989 mmol, Sigma-Aldrich Chemical Company, Inc.) in DCM (1.658 ml) to stir at room temperature for 5 h. Solvent was evaporated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (50 g), eluting with a gradient of 10% to 100% EtOAc in hexane. LCMS showed product was not isolated at ≧95%. The crude product was taken up in DCM and loaded onto an AccuBond SCX cartridge. The cartridge was rinsed with DCM followed by MeOH to remove impurities. The column was then rinsed with 2.0 ammonia in MeOH. The fractions were evaporated in vacuo. The residue was taken up in MeOH at which time a precipitate was noted to form. The round bottomed flask was placed in the freezer overnight. The solid was filtered from the filtrate and washed with cold MeOH to give the title compound (17.1 mg, 0.045 mmol, 9.13% yield). LCMS showed product peak at 1.757 min (m+1=377.0).

Workup

  1. customSolvent was evaporated in vacuo
  2. customchromatographed through a Biotage SNAP HP-silica gel column (50 g)
  3. washeluting with a gradient of 10% to 100% EtOAc in hexane
  4. customwas not isolated at ≧95%
  5. washThe cartridge was rinsed with DCM
  6. customto remove impurities
  7. washThe column was then rinsed with 2.0 ammonia in MeOH
  8. customThe fractions were evaporated in vacuo
  9. customto form
  10. customwas placed in the freezer overnight
  11. filtrationThe solid was filtered from the filtrate
  12. washwashed with cold MeOH

Sources & evidence

ORD record
ord-853352ccc8484be5bf4bfc63ce371dff
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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