Diisopropylethylamine → HCID 44540783, compound

HRID 1616005Notes

Reaction equation

HRID 1616005 reaction equation
[N:1]1([CH2:7][C:8]2[N:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH:50]1[C:58]2[C:53](=[C:54]([C:59]3[CH:60]=[C:61]([NH2:74])[C:62]4[C:66]([CH:67]=3)=[N:65][N:64](C3CCCCO3)[CH:63]=4)[CH:55]=[CH:56][CH:57]=2)[CH:52]=[CH:51]1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH:50]1[C:58]2[C:53](=[C:54]([C:59]3[CH:67]=[C:66]4[C:62]([CH:63]=[N:64][NH:65]4)=[C:61]([NH:74][C:14]([C:12]4[CH:11]=[CH:10][CH:9]=[C:8]([CH2:7][N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)[N:13]=4)=[O:16])[CH:60]=3)[CH:55]=[CH:56][CH:57]=2)[CH:52]=[CH:51]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58267987HCID 58267987, compoundHCID 582679956-(1H-Indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine

Product 1

HCID 44540783HCID 44540783, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-(4-morpholinylmethyl)-2-pyridinecarboxylic acid (33 mg, 0.15 mmol) in DMF (0.8 ml) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (72 mg, 0.19 mmol) and DIPEA (0.052 ml). After 5 minutes the resulting solution was added to 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (33 mg, 0.10 mmol). The mixture was stirred at room temperature for 15 mins then left to stand for 2 h. The reaction was treated with saturated sodium bicarbonate solution (10 ml) and extracted with dichloromethane (3×10 ml). The extracts were passed through a hydrophobic frit, combined and the solvent was evaporated under nitrogen flow. The residue was dissolved in methanol (1 ml) and hydrochloric acid (2M, 0.080 ml) was added. After about 1 hour the solvent was evaporated under a stream of nitrogen to give a crude product which was purified by Mass Directed Automated Preparative HPLC (Method B). Fractions containing pure product were evaporated under a nitrogen stream to give the title compound (11 mg) as a pale solid.

Workup

  1. waitthen left
  2. waitto stand for 2 h
  3. extractionextracted with dichloromethane (3×10 ml)
  4. customthe solvent was evaporated under nitrogen flow
  5. dissolutionThe residue was dissolved in methanol (1 ml)
  6. additionhydrochloric acid (2M, 0.080 ml) was added
  7. customAfter about 1 hour the solvent was evaporated under a stream of nitrogen
  8. customto give a crude product which
  9. customwas purified by Mass Directed Automated Preparative HPLC (Method B)
  10. additionFractions containing pure product
  11. customwere evaporated under a nitrogen stream

Sources & evidence

ORD record
ord-2ee5f6716bf04ebcb41e6ac7e11ed92e
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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