Triethylamine → HCID 58138839, compound

HRID 2382948Notes

Reaction equation

HRID 2382948 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([NH:19][CH2:20][C:21]4[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=4)[C:24](O)=[O:25])=[O:18])[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C[CH2:31][N:32](CC)CC.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.CN>CN(C=O)C.[Cl-].[NH4+]>[CH3:31][NH:32][C:24]([C:23]1[CH:22]=[C:21]([CH:29]=[CH:28][CH:27]=1)[CH2:20][NH:19][C:17]([C:12]1[C:11]2[CH:10]=[N:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1)=[O:18])=[O:25]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 6364545Methylamine hydrochlorideHCID 58138764HCID 58138764, compound

Product 1

HCID 58138839HCID 58138839, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 3-({[1-(4-fluoro-phenyl)-1H-indazole-4-carbonyl]-amino}-methyl)-benzoic acid (70 mg, 0.2 mmol) in DMF (5 mL) was added Et3N (0.07 mL, 0.6 mmol) and PyBOP (100 mg, 0.2 mmol). After 15 minutes of stirring at room temperature, methylamine hydrochloride (15 mg, 0.22 mmol) was added. After 16 hours, the mixture was diluted with saturated aqueous ammonium chloride (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate (20 mL), brine (20 mL) and dried over sodium sulfate. The crude product was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes. The material from the column was then crystallized from EtOAc/ether/hexanes to afford the title compound as a white solid.

Workup

  1. waitAfter 16 hours
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate (20 mL), brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of 0-100% ethyl acetate in hexanes
  7. customThe material from the column was then crystallized from EtOAc/ether/hexanes

Sources & evidence

ORD record
ord-25389062aa8046e49814018cb9253b3c
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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