HCID 22064356, compound → HCID 11450854, compound

HRID 1827874Notes

Reaction equation

HRID 1827874 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][CH2:8][CH2:9][NH:10]C(=O)OC(C)(C)C)=[C:4]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[N:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=2)=[O:22])[CH:3]=1>FC(F)(F)C(O)=O.ClCCl>[NH2:10][CH2:9][CH2:8][CH2:7][O:6][C:5]1[CH:18]=[CH:19][C:2]([Cl:1])=[CH:3][C:4]=1[NH:20][C:21]([NH:23][C:24]1[CH:29]=[N:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=1)=[O:22]

Participants

4

Reactant 1

HCID 22064356HCID 22064356, compound

Product 1

HCID 11450854HCID 11450854, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Example 38A in trifluoroacetic acid (0.1 mL) and dichloromethane (0.9 mL) was stirred at room temperature for 3 hours and concentrated. The concentrate was purified by HPLC with acetonitrile/water containing 0.1% TFA to provide 2.8 mg (6%) of the desired product. MS (ESI(−)) m/z 347 (M−H)−; 1H NMR (500 MHz, DMSO-d6) δ 10.93 (br s, 1H), 10.09 (br s, 1H), 8.91 (s, 1H), 8.85 (s, 1H), 8.26 (d, J=2.5 Hz, 1H), 7.71 (br s, 2H), 7.12 (dd, J=8.7, 2.2 Hz, 1H), 7.10 (d, J=8.7 Hz, 1H), 4.20 (t, J=6.2 Hz, 2H), 3.03 (br s, 2H), 2.10 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by HPLC with acetonitrile/water containing 0.1% TFA

Sources & evidence

ORD record
ord-8e6e94680abe45aa8c0c6873bc5a3785
Source dataset
uspto-grants-2006_06
Patent number
US07056925B2

Reaction notes

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