4-Chloro-2-fluoroaniline → HCID 57650482, compound

HRID 2063498Notes

Reaction equation

HRID 2063498 reaction equation
CO[C:3]1[C:6](=O)[C:5](=[O:8])[C:4]=1[O:9]C.[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([F:19])[CH:13]=1.Cl.[Cl:21][C:22]1[CH:39]=[CH:38][C:25]([CH2:26][N:27]2[C:31]([C@H:32]3[CH2:36][CH2:35][CH2:34][NH:33]3)=[N:30][N:29]=[C:28]2[CH3:37])=[CH:24][CH:23]=1>CO.CCN(C(C)C)C(C)C>[Cl:21][C:22]1[CH:39]=[CH:38][C:25]([CH2:26][N:27]2[C:28]([CH3:37])=[N:29][N:30]=[C:31]2[C@H:32]2[CH2:36][CH2:35][CH2:34][N:33]2[C:3]2[C:4](=[O:9])[C:5](=[O:8])[C:6]=2[NH:16][C:15]2[CH:17]=[CH:18][C:12]([Cl:11])=[CH:13][C:14]=2[F:19])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 938984-Chloro-2-fluoroanilineHCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 688114841140496-10-1

Product 1

HCID 57650482HCID 57650482, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
75 °C

Procedure

Dimethoxycyclobutenedione (28 mg) and the 4-chloro-2-fluoroaniline (30 mg) were dissolved in methanol (1 ml) and DIEA (0.035 ml). The reaction was stirred at 75° C. overnight. (R)-4-(4-chlorobenzyl)-3-methyl-5-(pyrrolidin-2-yl)-4H-1,2,4-triazole hydrochloride (58 mg) was added and stirring and heating was continued overnight. Flash chromatography purification (0-10% methanol/DCM) afforded the desired product as residue (11 mg, 11%).

Workup

  1. stirringstirring
  2. temperatureheating
  3. waitwas continued overnight
  4. customFlash chromatography purification (0-10% methanol/DCM)

Sources & evidence

ORD record
ord-2348d00fa0294a20baea7e9931615711
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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