3-Fluorobenzoyl chloride → HCID 67307066, compound

HRID 1013552Notes

Reaction equation

HRID 1013552 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:14]2[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].CCN(C(C)C)C(C)C.[F:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](Cl)=[O:36]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:14]2[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[C:6]=1[C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])=[O:36]

Participants

6

Reactant 3

HCID 743763-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 58337841HCID 58337841, compound

Product 1

HCID 67307066HCID 67307066, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 16 (31 mg 0.1 mmol) in DCM (5 ml) was added DIEA (0.052 ml, 0.3 mmole), 3-fluorobenzoyl chloride (0.018 ml, 0.15 mmol) and catalytic amount of DMAP. The mixture was stirred at rt for 17 hrs, diluted with DCM (15 ml), washed with water, saturated sodium bicarbonate (aq.), water, 10% citric acid (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 used in the next step without further purification. LC-MS for C22H21FN2O4S: 428; found: 429.

Workup

  1. washwashed with water, saturated sodium bicarbonate (aq.), water, 10% citric acid (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 used in the next step without further purification

Sources & evidence

ORD record
ord-0773c597fed14a36b15d84c055180f02
Source dataset
uspto-grants-2011_07
Patent number
US07981925B2

Reaction notes

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