3-Chloroaniline → HCID 67044200, compound

HRID 2367091Notes

Reaction equation

HRID 2367091 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([C:14]3[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=3[C:16]([OH:18])=O)=[O:13])[CH:9]=2)[NH:4][CH2:3]1.C1C=NC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[Cl:64][C:65]1[CH:66]=[C:67]([CH:69]=[CH:70][CH:71]=1)[NH2:68]>CN(C)C=O>[Cl:64][C:65]1[CH:66]=[C:67]([N:68]2[C:16](=[O:18])[C:15]3[C:14](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]2([C:8]2[CH:9]=[C:10]3[C:5]([NH:4][CH2:3][C:2](=[O:1])[NH:11]3)=[CH:6][CH:7]=2)[OH:13])[CH:69]=[CH:70][CH:71]=1

Participants

7

Reactant 5

HCID 79323-ChloroanilineHCID 79724-MethylmorpholineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67044479HCID 67044479, compound

Product 1

HCID 67044200HCID 67044200, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid (50 mg, 0.16 mmol) in N,N-dimethylformamide (2.0 mL), HOAt (40 mg, 0.28 mmol), HATU (90 mg, 0.23 mmol) and NMM (0.1 mL, 0.80 mmol) was added and the reaction mixture was stirred for 20 minutes at room temperature, followed by the addition of 3-chloro-aniline (24 μL, 0.23 mmol). The reaction mixture was stirred for 15 hours at room temperature. The solvent was evaporated and the resulting crude was purified by reverse phase preparative HPLC (CH3CN/H2O with 0.1% TFA). The fractions were collected and the aqueous solution was lyophilized to give 7-[2-(3-chlorophenyl)-1-hydroxy-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-3,4-dihydroquinoxalin-2(1H)-one (36 mg, 39% yield.). 1H NMR (400 MHz, DMSO-d6): 12.25 (s, 1H), 10.44 (s, 1H), 8.04 (d, 1H), 7.78 (t, 1H), 7.59 (d, 1H), 7.47 (m, 2H), 7.43 (dd, 1H), 7.33 (m, 3H), 7.08 (m, 3H), 4.22 (s, 2H); MS (EI) for C22H16ClN3O3: 406 (MH+).

Workup

  1. stirringThe reaction mixture was stirred for 15 hours at room temperature
  2. customThe solvent was evaporated
  3. customthe resulting crude was purified by reverse phase preparative HPLC (CH3CN/H2O with 0.1% TFA)
  4. customThe fractions were collected

Sources & evidence

ORD record
ord-4dce7d2937144851929a0fd62e94d360
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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