3-Fluorobenzoyl chloride → HCID 59225729, compound

HRID 387504Notes

Reaction equation

HRID 387504 reaction equation
[NH2:1][C:2]1[S:6][CH:5]=[C:4]([CH:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:8]2)[C:3]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24].CCN(C(C)C)C(C)C.[F:37][C:38]1[CH:39]=[C:40]([CH:44]=[CH:45][CH:46]=1)[C:41](Cl)=[O:42]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:26]([O:25][C:23]([C:3]1[C:4]([CH:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:8]2)=[CH:5][S:6][C:2]=1[NH:1][C:41](=[O:42])[C:40]1[CH:44]=[CH:45][CH:46]=[C:38]([F:37])[CH:39]=1)=[O:24])[CH3:27]

Participants

6

Reactant 3

HCID 743763-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 58337784HCID 58337784, compound

Product 1

HCID 59225729HCID 59225729, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 55 (˜2 mmol) in DCM (10 ml) was added DIEA (0.7 ml, 4 mmol), 3-fluorobenzoyl chloride (0.48 ml, 4 mmol) and catalytic amount of DMAP. The mixture was stirred at rt for 17 hrs, diluted with DCM (50 ml), washed with water, saturated sodium bicarbonate (aq.), water, 1N HCl (aq.) and brine, dried over anhydrous sodium sulfate. The drying agent was removed by filtration. The filtrate was concentrated under vacuum. The crude product was purified on a silica gel column to give 56 as a yellow oil (0.48 g). LC-MS for C27H27FN2O5S: 510; found: 511.

Workup

  1. washwashed with water, saturated sodium bicarbonate (aq.), water, 1N HCl (aq.) and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe drying agent was removed by filtration
  4. concentrationThe filtrate was concentrated under vacuum
  5. customThe crude product was purified on a silica gel column

Sources & evidence

ORD record
ord-e3cafac5d99a45d69cd53a408781af0b
Source dataset
uspto-grants-2013_02
Patent number
US08372991B2

Reaction notes

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