Diisopropylethylamine → HCID 86670725, compound

HRID 878096Notes

Reaction equation

HRID 878096 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:6]([N:8]([CH2:22][C:23](O)=[O:24])[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])=[O:7].C[CH2:36][N:37](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CN.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N:8]([CH2:22][C:23](=[O:24])[NH:37][CH3:36])[C:6](=[O:7])[C:5]1[CH:4]=[C:3]([C:2]([F:34])([F:1])[F:33])[CH:28]=[C:27]([C:29]([F:31])([F:30])[F:32])[CH:26]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86670726{(3,5-Bis-trifluoromethyl-benzoyl)-[4-(2-chloro-phenyl)-pyridin-3-yl]-amino}-acetic acid

Product 1

HCID 86670725HCID 86670725, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {(3,5-bis-trifluoromethyl-benzoyl)-[4-(2-chloro-phenyl)-pyridin-3-yl]-amino}-acetic acid (100 mg, 199 μmol) in DMF (2 mL) was added DIPEA (129 mg, 169 μL, 994 μmol), HATU (91.5 mg, 239 μmol) and methylamine hydrochloride (16.1 mg, 239 μmol). The reaction mixture was stirred at room temperature for 2 hours and then poured on 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc. The layers were separated and the aqueous layer was extracted a second time with 30 mL EtOAc. The organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless solid (67 mg, 65%). MS (ESI): m/z=516.091 [M+H]+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted a second time with 30 mL EtOAc
  3. washThe organic layers were washed with 30 mL brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe compound was purified by silica gel chromatography
  8. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-885aa9d69b5a4947b5529af6c3153108
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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