Diisopropylethylamine → (R)-2-(2-(4-Chlorobenzyl)-2H-1,2,4-triazol-3-yl)-N-((S)-7-(trifluoromethyl)chroman-4-yl)pyrrolidine-1-carboxamide

HRID 2063480Notes

Reaction equation

HRID 2063480 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:11]([C@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:17](Cl)=[O:18])=[N:10][CH:9]=[N:8]2)=[CH:4][CH:3]=1.[NH2:22][C@@H:23]1[C:32]2[C:27](=[CH:28][C:29]([C:33]([F:36])([F:35])[F:34])=[CH:30][CH:31]=2)[O:26][CH2:25][CH2:24]1.CCN(C(C)C)C(C)C>CC#N>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:11]([C@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:17]([NH:22][C@@H:23]3[C:32]4[C:27](=[CH:28][C:29]([C:33]([F:36])([F:34])[F:35])=[CH:30][CH:31]=4)[O:26][CH2:25][CH2:24]3)=[O:18])=[N:10][CH:9]=[N:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 46911908(S)-7-(trifluoromethyl)chroman-4-amineHCID 57650104(R)-1-(4-chlorobenzyl)-5-(1-chlorocarbonylpyrrolidin-2-yl)-1H-1,2,4-triazole

Product 1

HCID 57650063(R)-2-(2-(4-Chlorobenzyl)-2H-1,2,4-triazol-3-yl)-N-((S)-7-(trifluoromethyl)chroman-4-yl)pyrrolidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (R)-1-(4-chlorobenzyl)-5-(1-chlorocarbonylpyrrolidin-2-yl)-1H-1,2,4-triazole (60 mg), (S)-4-amino-7-trifluoromethylchroman and DIEA in dry MeCN was stirred overnight at RT. The solvent was removed and the residue was partitioned between water and EtOAc. The EtOAc layer was washed with water and evaporated after drying over Na2SO4. The residue was purified by chromatography (silica gel, hexane:EtOAc (1:1)→EtOAc) to give 40 mg of the desired product.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between water and EtOAc
  3. washThe EtOAc layer was washed with water
  4. customevaporated
  5. dry with materialafter drying over Na2SO4
  6. customThe residue was purified by chromatography (silica gel, hexane:EtOAc (1:1)→EtOAc)

Sources & evidence

ORD record
ord-6d3f29519aaf4e2c8b1a36fb463ab841
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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