Propargylamine → HCID 23577872, compound

HRID 1827457Notes

Reaction equation

HRID 1827457 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15]3[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=3[C:17](O)=[O:18])=[CH:11][CH:12]=2)[N:7]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[N:6]=1)=[O:4].[CH2:30]([NH2:33])[C:31]#[CH:32].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O.O>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15]3[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=3[C:17](=[O:18])[NH:33][CH2:30][C:31]#[CH:32])=[CH:11][CH:12]=2)[N:7]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[N:6]=1)=[O:4]

Participants

7

Reactant 3

HCID 239041PropargylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23577846HCID 23577846, compound

Product 1

HCID 23577872HCID 23577872, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[3-Methylcarbamoyl-1-(tetrahydro-pyran-2-yl)-1H-indazol-6-ylamino]-benzoic acid (150 mg, 0.381 mmol) in DMF (3.6 mL) was added propargylamine (0.052 mL, 0.761 mmol), triethylamine(TEA) (0.264 mL, 1.90 mmol), and HATU (217 mg, 0.571 mmol). The reaction was stirred for 4 hours, and then diluted with EtOAc (30 mL) and water (30 mL). The layers were separated, and the aqueous was extracted with EtOAc (2×20 mL). The combined organics were washed with saturated NaCl (15 mL) and then dried over Na2SO4. The solids were removed by filtration, and the liquid was concentrated by rotary evaporation to a yellow oil (164 mg, 100%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous was extracted with EtOAc (2×20 mL)
  3. washThe combined organics were washed with saturated NaCl (15 mL)
  4. dry with materialdried over Na2SO4
  5. customThe solids were removed by filtration
  6. concentrationthe liquid was concentrated by rotary evaporation to a yellow oil (164 mg, 100%)

Sources & evidence

ORD record
ord-b4f8efd284614d63897a87e63c0ab2d4
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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