Trifluoroacetic acid → HCID 118307490, compound

HRID 1497345Notes

Reaction equation

HRID 1497345 reaction equation
[O:1]=[C:2]1[NH:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[CH:8]=2)[NH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl.C1COCC1>[N:12]1([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C:2](=[O:1])[NH:11][CH2:10]3)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118317160HCID 118317160, compound

Product 1

HCID 118307490HCID 118307490, compoundYield 134.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 10 (0.7 g, 2.11 mmol) in a mixture of CH2Cl2 (15 mL) and THF (5 mL) at 0° C. was added TFA (5 mL) and the mixture was stirred at room temperature for 6 h. The solvent was evaporated under vacuum to afford 0.66 g (96%) of compound 6 as a dark brown gum. 1H NMR (500 MHz, DMSO-d6) δ=3.17 (m, 4H, 2CH2), 3.40 (m, 4H, 2CH2), 4.28 (s, 2H, CH2), 6.70 (m, 2H, aromatic-H), 6.73 (m, 1H, aromatic-H), 8.81 (br. s, 1H, NH), 8.86 (br. s, 1H, NH). 13C NMR (125.7 MHz, DMSO-d6) δ=46.11 (CH2), 46.70 (CH2), 48.68 (CH2), 112.21 (aromatic-C), 112.27 (aromatic-C), 117.31 (aromatic-C), 130.28 (aromatic-C), 134.99 (aromatic-C), 143.38 (aromatic-C), 154.82 (C═O). Calculated (%) for C14H16F3N4O2 (329.12); C, 51.06; H, 4.90; N, 17.01. found (%); C, 51.01; H, 4.95; N, 16.95.

Workup

  1. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-df876cbb817745d1ac5a1a02858eadb9
Source dataset
uspto-grants-2015_12
Patent number
US09199969B1

Reaction notes

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