Acetyl chloride → HCID 59216004, compound

HRID 2245267Notes

Reaction equation

HRID 2245267 reaction equation
[OH:1][CH:2]1[CH2:6][NH:5][CH2:4][CH:3]1[NH:7][C:8]([C:10]1[C:14]([CH3:15])=[C:13](/[CH:16]=[C:17]2\[C:18](=[O:27])[NH:19][C:20]3[C:25]\2=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[NH:12][C:11]=1[CH3:28])=[O:9].CCN(C(C)C)C(C)C.[CH3:38][C:39](Cl)=[O:40]>>[C:39]([N:5]1[CH2:6][CH:2]([OH:1])[CH:3]([NH:7][C:8]([C:10]2[C:14]([CH3:15])=[C:13](/[CH:16]=[C:17]3\[C:18](=[O:27])[NH:19][C:20]4[C:25]\3=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[NH:12][C:11]=2[CH3:28])=[O:9])[CH2:4]1)(=[O:40])[CH3:38]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67410238HCID 67410238, compound

Product 1

HCID 59216004HCID 59216004, compoundYield 57%

Procedure

To the solution of 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (4-hydroxy-pyrrolidin-3-yl)-amide (150 mg, 0.39 mmol) and DIEA (89 mg, 0.69 mmol) was added CH3COCl (33.7 mg, 0.43 mmol) on an ice bath. The mixture was stirred at r.t. for 3 hrs. After the reaction was complete, DMF was evaporated under reduced pressure and the residue was triturated with methanol and the solid was collected by filtration, washed with ethanol and dried in vacuum to give title compound (82 mg, 57% yield) as an orange solid. 1H NMR (300 MHz, DMSO-d6): δ=13.67 (s, 1H), 10.87 (s, 1H), 8.07-8.10 (d, 1H), 7.71-7.85 (m, 3H), 6.82-6.92 (m, 2H), 5.34-5.44 (dd, 1H), 4.13-4.18 (d, 2H), 3.67-3.81 (m, 4H), 2.38-2.40 (ds, 6H), 1.92-1.93 (d, 3H). LC/MS: 427.0 [M+H]+.

Workup

  1. customDMF was evaporated under reduced pressure
  2. customthe residue was triturated with methanol
  3. filtrationthe solid was collected by filtration
  4. washwashed with ethanol
  5. customdried in vacuum

Sources & evidence

ORD record
ord-0240f68eb6d948d5862dbc49e143a447
Source dataset
uspto-grants-2010_03
Patent number
US07683057B2

Reaction notes

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