Diisopropylethylamine → 3-({(1S)-2-[(Difluoromethyl)oxy]-1-methylethyl}oxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide

HRID 2425496Notes

Reaction equation

HRID 2425496 reaction equation
CCN(C(C)C)C(C)C.[F:10][CH:11]([F:34])[O:12][CH2:13][C@@H:14]([O:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)[C:20]([OH:22])=O)[CH3:15].[CH3:35][N:36]1[CH:40]=[CH:39][C:38]([NH2:41])=[N:37]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[F:34][CH:11]([F:10])[O:12][CH2:13][C@@H:14]([O:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)[C:20]([NH:41][C:38]1[CH:39]=[CH:40][N:36]([CH3:35])[N:37]=1)=[O:22])[CH3:15]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1372541-Methyl-3-aminopyrazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 591271733-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-phenylmethoxy-benzoic acid

Product 1

HCID 536296413-({(1S)-2-[(Difluoromethyl)oxy]-1-methylethyl}oxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DIPEA (0.198 mL, 1.14 mmol) was added to a mixture of 3-[(2S)-1-(difluoromethoxy) propan-2-yl]oxy-5-phenylmethoxy-benzoic acid (0.10 g, 0.28 mmol), 1-methylpyrazol-3-amine (CAS no. 1904-31-0) (39 mg, 0.4 mmol) and HATU (0.227 g, 0.6 mmol) in DMF (3 mL) and stirred at RT for 20 hours. Ethyl acetate (30 mL) was added and the mixture washed with water (30 mL), brine (30 mL), dried (MgSO4), filtered and reduced in vacuo. The residue was chromatographed on silica, eluting with a gradient of 0-100% ethyl acetate in isohexane, to give the desired compound (0.1 g).

Workup

  1. washthe mixture washed with water (30 mL), brine (30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe residue was chromatographed on silica
  5. washeluting with a gradient of 0-100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-0c8d5feae7d64755ac2c73b875fa5c78
Source dataset
uspto-grants-2011_06
Patent number
US07964725B2

Reaction notes

Loading…