HCID 66580009, compound → HCID 66580078, compound

HRID 1476199Notes

Reaction equation

HRID 1476199 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:19][C:20]3[O:21][C:22]4[C:27]([C:28](=[O:36])[C:29]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C)[CH:12]=3)[C:3]=12>ClCCl.B(Br)(Br)Br>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:19][C:20]3[O:21][C:22]4[C:27]([C:28](=[O:36])[C:29]=3[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=3)[C:3]=12

Participants

4

Reactant 1

HCID 66580009HCID 66580009, compound

Product 1

HCID 66580078HCID 66580078, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

To a solution of example 52 (0.150 g, 0.315 mmoles) in dichloromethane (30 ml), BBr3 (1M in dichloromethane, 1.5 ml) was added at 0° C. and the reaction mixture was warmed to RT and then stirred for 12 h. The reaction mixture was quenched with 1.5N HCl solution and extracted with dichloromethane. The organic layer was dried over sodium sulphate and concentrated. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as light yellow solid (0.040 g, 27% yield). MP: 154-158° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 9.69(s,1H), 8.22(s,1H), 8.06(dd, J=7.8,1.2 Hz, 1H), 7.49(t, J=7.3 Hz, 1H), 7.44(d, J=8.5 Hz, 1H), 7.37-7.29(m, 6H), 7.03 (d, J=7.9Hz, 2H), 6.86(dd, J=8.3,1.6 Hz, 1H), 5.49(s, 2H). Mass: 462.03(M++1).

Workup

  1. customThe reaction mixture was quenched with 1.5N HCl solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-66ae5f77529a4d7b9fb95fc0452cb6cf
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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