3-Fluorobenzoyl chloride → HCID 67307066, compound

HRID 387497Notes

Reaction equation

HRID 387497 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-b91e72e334794edd93505751288b5eaa
Source dataset
uspto-grants-2013_02
Patent number
US08372991B2

Reaction notes

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