Triethylamine → HCID 86703134, compound

HRID 2204327Notes

Reaction equation

HRID 2204327 reaction equation
CCCP(=O)=O.[Cl:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=O)=[C:10]([N:17]2[C:24](=[O:25])[C:23]3[CH:22]=[CH:21][N:20]([CH:26]([CH3:28])[CH3:27])[C:19]=3[CH:18]2[C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[CH:9]=1.CCN(CC)CC>CCOC(C)=O>[Cl:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]#[N:14])=[C:10]([N:17]2[C:24](=[O:25])[C:23]3[CH:22]=[CH:21][N:20]([CH:26]([CH3:28])[CH3:27])[C:19]=3[CH:18]2[C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16167369Propylphosphoric anhydrideHCID 86703135HCID 86703135, compound

Product 1

HCID 86703134HCID 86703134, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of propylphosphonic anhydride (T3P/PPA) (50% in EtOAc) (7.13 mmol) was added dropwise to a solution of 4-chloro-2-[6-(4-chloro-phenyl)-1-isopropyl-4-oxo-4,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-5-yl]benzamide (Step AB2) (3.10 mmol) and Et3N (3.41 mmol) in EtOAc (25 mL) at 45° C. After 23 h, the reaction mixture was cooled to rt and partitioned between EtOAc and H2O. The organice phase was successively washed with a saturated aqueous solution of NaHCO3, water and brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a white solid. tR: 4.97 min (HPLC 1); ESI-MS: tR=1.19 min, [M+H]+ 410/412/414 (LC-MS 1); TLC: Rf=0.16 (1:3 EtOAc/heptanes).

Workup

  1. custompartitioned between EtOAc and H2O
  2. washThe organice phase was successively washed with a saturated aqueous solution of NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-6db4354f2d404e009abdf442b0e75c18
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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