Diisopropylethylamine → HCID 67116196, compound

HRID 243843Notes

Reaction equation

HRID 243843 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[N:15]=[CH:14][CH:13]=[N:12]2)[C:3]=1[C:4]([OH:6])=O.[C:16]([O:20][C:21]([N:23]1[CH2:30][CH:29]2[CH:25]([CH2:26][NH:27][CH2:28]2)[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[C:16]([O:20][C:21]([N:23]1[CH2:24][CH:25]2[CH:29]([CH2:28][N:27]([C:4](=[O:6])[C:3]3[C:7]([N:11]4[N:15]=[CH:14][CH:13]=[N:12]4)=[CH:8][CH:9]=[CH:10][C:2]=3[F:1])[CH2:26]2)[CH2:30]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 670866272-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid

Product 1

HCID 67116196HCID 67116196, compoundYield 19.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Fluoro-6-[1,2,3]triazol-2-yl-benzoic acid (0.97 g, 4.71 mmol), hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (Intermediate 15, 1.0 g, 4.71 mmol), HATU (2.68 g, 7.06 mmol), in DMF (18.8 mL) was added DIEA (2.43 mL, 14.13 mmol). The mixture was stirred at rt for 1 hr. The mixture was diluted with EtOAc and washed with water. The aqueous layer was extracted with EtOAc, the organic layers were combined, dried (Na2SO4), filtered and concentrated to provide the crude product. Purification (FCC) (5-50% of a solution 10% MeOH, 0.1% NH4OH in DCM/EtOAc over 25 minutes, and 50-100% from 25-35 minutes) provided 5-(2-fluoro-6-[1,2,3]triazol-2-yl-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (0.376 g, 19.5%).

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide the crude product
  7. customPurification (FCC) (5-50% of a solution 10% MeOH, 0.1% NH4OH in DCM/EtOAc over 25 minutes, and 50-100% from 25-35 minutes)

Sources & evidence

ORD record
ord-2857886bea1044749f88ece06600baf1
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

Loading…