Acetyl chloride → HCID 59216004, compound

HRID 38035Notes

Reaction equation

HRID 38035 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-6cf3062837bf4900ae8c604dcd737540
Source dataset
uspto-grants-2013_09
Patent number
US08524709B2

Reaction notes

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