Trifluoroacetic acid → HCID 54575427, compound

HRID 2096285Notes

Reaction equation

HRID 2096285 reaction equation
[NH2:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][C:7]2[N:12]3[CH:13]=[C:14]([C:16]4[C:24]5[C:19](=[N:20][CH:21]=[CH:22][CH:23]=5)[NH:18][CH:17]=4)[CH:15]=[C:11]3[C:10](=[O:25])[N:9](CC3C=CC(OC)=CC=3OC)[CH:8]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:12]3[CH:13]=[C:14]([C:16]4[C:24]5[C:19](=[N:20][CH:21]=[CH:22][CH:23]=5)[NH:18][CH:17]=4)[CH:15]=[C:11]3[C:10](=[O:25])[NH:9][CH:8]=2)=[CH:37][CH:38]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67441940HCID 67441940, compound

Product 1

HCID 54575427HCID 54575427, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of EXAMPLE 23J (300 mg, 0.594 mmol) in CH2Cl2 (5 ml) was added trifluoroacetic acid (10 mL), and the mixture was heated at 120° C. in a microwave reactor (Biotage, Initiator) for 40 minutes. After cooling, the reaction mixture was diluted with toluene (50 mL) and concentrated. The residue was purified flash chromatography (CH2Cl2/tetrahydrofuran/CH3OH/Et3N, 50/50/1/1) to afford the title compound. LC-MS (ESI): m/z 356 (M+H), RT: 1.30 min; 1H NMR (400 MHz, dimethylsulfoxide, d6): δ 3.92 (s, 2H), 4.97 (s, 2H), 6.28 (d, J=5.6 Hz, 1H), 6.54 (d, J=8.0 Hz, 2H), 7.07 (d, J=8.4 Hz, 2H), 7.13 (dd, J=4.8, 3.2 Hz, 1H), 7.27 (d, J=2.0 Hz, 1H), 7.69 (d, J=2.0 Hz, 1H), 7.83 (d, J=2.4 Hz, 1H), 8.18 (dd, J=6.8, 1.2 Hz, 1H), 8.27 (dd, J=3.6, 1.2 Hz, 1H), 10.46 (d, J=6.0 Hz, 1H), 11.74 (br s, 1H).

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrated
  3. customThe residue was purified flash chromatography (CH2Cl2/tetrahydrofuran/CH3OH/Et3N, 50/50/1/1)

Sources & evidence

ORD record
ord-2924ce2b04fc44b9b44498007742047c
Source dataset
uspto-grants-2013_05
Patent number
US08450320B2

Reaction notes

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