Pyridine → HCID 57900472, compound

HRID 84709Notes

Reaction equation

HRID 84709 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][C:6]3[CH:12]=[C:13]([C:15](Cl)=[O:16])[S:14][C:5]=3[C:4]=2[CH:3]=1.[F:18][C:19]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:20]=1[NH2:21].N1C=CC=C[CH:28]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:18][C:19]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:20]=1[N:21]([CH3:28])[C:15]([C:13]1[S:14][C:5]2[C:4]3[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:9]=3[O:8][CH2:7][C:6]=2[CH:12]=1)=[O:16]

Participants

6

Reactant 3

HCID 1049PyridineHCID 97092,4-DifluoroanilineHCID 57900471HCID 57900471, compound

Product 1

HCID 57900472HCID 57900472, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a reaction vial charged with 8-fluoro-4H-thieno[3,2-c]chromene-2-carbonyl chloride (0.120 g, 0.447 mmol) and 2,4-difluoroaniline (0.0959 g, 0.670 mmol) was added a catalytic amount of DMAP. Pyridine in methylene chloride (1.2 M, 1.49 mL) was added. The reaction was stirred at room temperature with LC/MS monitor. The reaction was complete in a couple hours. After aqueous work up, the reaction was concentrated in vacuo, taken into DMF at a concentrated of 100 mg/ml and purified by preparative RP-HPLC to give 163bp. Yield=31% of theoretical. MS: (ESI+)=376.4

Workup

  1. customTo a reaction
  2. concentrationAfter aqueous work up, the reaction was concentrated in vacuo
  3. concentrationa concentrated of 100 mg/ml
  4. custompurified by preparative RP-HPLC
  5. customto give 163bp

Sources & evidence

ORD record
ord-224fa7364aef4432bf3e754eeb32b113
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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